New mechanistic approach in the enamine-based asymmetric organocatalysis

Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not pos...
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Gespeichert in:

Autor*in:	Gurka, András A. [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	Aldol reaction Enamine Transition state Dual stereocontrol Enantioselectivity

Anmerkung:	© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022

Übergeordnetes Werk:	Enthalten in: Structural chemistry - Dordrecht : Springer Science Business Media B.V., 1990, 34(2022), 1 vom: 04. Mai, Seite 83-86
Übergeordnetes Werk:	volume:34 ; year:2022 ; number:1 ; day:04 ; month:05 ; pages:83-86

Links:	Volltext

DOI / URN:	10.1007/s11224-022-01952-w

Katalog-ID:	SPR04914295X

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520			\|a Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule.
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allfields	10.1007/s11224-022-01952-w doi (DE-627)SPR04914295X (SPR)s11224-022-01952-w-e DE-627 ger DE-627 rakwb eng Gurka, András A. verfasserin aut New mechanistic approach in the enamine-based asymmetric organocatalysis 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022 Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule. Aldol reaction (dpeaa)DE-He213 Enamine (dpeaa)DE-He213 Transition state (dpeaa)DE-He213 Dual stereocontrol (dpeaa)DE-He213 Enantioselectivity (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2022), 1 vom: 04. Mai, Seite 83-86 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2022 number:1 day:04 month:05 pages:83-86 https://dx.doi.org/10.1007/s11224-022-01952-w lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2022 1 04 05 83-86
spelling	10.1007/s11224-022-01952-w doi (DE-627)SPR04914295X (SPR)s11224-022-01952-w-e DE-627 ger DE-627 rakwb eng Gurka, András A. verfasserin aut New mechanistic approach in the enamine-based asymmetric organocatalysis 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022 Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule. Aldol reaction (dpeaa)DE-He213 Enamine (dpeaa)DE-He213 Transition state (dpeaa)DE-He213 Dual stereocontrol (dpeaa)DE-He213 Enantioselectivity (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2022), 1 vom: 04. Mai, Seite 83-86 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2022 number:1 day:04 month:05 pages:83-86 https://dx.doi.org/10.1007/s11224-022-01952-w lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2022 1 04 05 83-86
allfields_unstemmed	10.1007/s11224-022-01952-w doi (DE-627)SPR04914295X (SPR)s11224-022-01952-w-e DE-627 ger DE-627 rakwb eng Gurka, András A. verfasserin aut New mechanistic approach in the enamine-based asymmetric organocatalysis 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022 Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule. Aldol reaction (dpeaa)DE-He213 Enamine (dpeaa)DE-He213 Transition state (dpeaa)DE-He213 Dual stereocontrol (dpeaa)DE-He213 Enantioselectivity (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2022), 1 vom: 04. Mai, Seite 83-86 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2022 number:1 day:04 month:05 pages:83-86 https://dx.doi.org/10.1007/s11224-022-01952-w lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2022 1 04 05 83-86
allfieldsGer	10.1007/s11224-022-01952-w doi (DE-627)SPR04914295X (SPR)s11224-022-01952-w-e DE-627 ger DE-627 rakwb eng Gurka, András A. verfasserin aut New mechanistic approach in the enamine-based asymmetric organocatalysis 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022 Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule. Aldol reaction (dpeaa)DE-He213 Enamine (dpeaa)DE-He213 Transition state (dpeaa)DE-He213 Dual stereocontrol (dpeaa)DE-He213 Enantioselectivity (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2022), 1 vom: 04. Mai, Seite 83-86 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2022 number:1 day:04 month:05 pages:83-86 https://dx.doi.org/10.1007/s11224-022-01952-w lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2022 1 04 05 83-86
allfieldsSound	10.1007/s11224-022-01952-w doi (DE-627)SPR04914295X (SPR)s11224-022-01952-w-e DE-627 ger DE-627 rakwb eng Gurka, András A. verfasserin aut New mechanistic approach in the enamine-based asymmetric organocatalysis 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022 Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule. Aldol reaction (dpeaa)DE-He213 Enamine (dpeaa)DE-He213 Transition state (dpeaa)DE-He213 Dual stereocontrol (dpeaa)DE-He213 Enantioselectivity (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2022), 1 vom: 04. Mai, Seite 83-86 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2022 number:1 day:04 month:05 pages:83-86 https://dx.doi.org/10.1007/s11224-022-01952-w lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2022 1 04 05 83-86
language	English
source	Enthalten in Structural chemistry 34(2022), 1 vom: 04. Mai, Seite 83-86 volume:34 year:2022 number:1 day:04 month:05 pages:83-86
sourceStr	Enthalten in Structural chemistry 34(2022), 1 vom: 04. Mai, Seite 83-86 volume:34 year:2022 number:1 day:04 month:05 pages:83-86
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	Aldol reaction Enamine Transition state Dual stereocontrol Enantioselectivity
isfreeaccess_bool	false
container_title	Structural chemistry
authorswithroles_txt_mv	Gurka, András A. @@aut@@
publishDateDaySort_date	2022-05-04T00:00:00Z
hierarchy_top_id	31886276X
id	SPR04914295X
language_de	englisch
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author	Gurka, András A.
spellingShingle	Gurka, András A. misc Aldol reaction misc Enamine misc Transition state misc Dual stereocontrol misc Enantioselectivity New mechanistic approach in the enamine-based asymmetric organocatalysis
authorStr	Gurka, András A.
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topic_title	New mechanistic approach in the enamine-based asymmetric organocatalysis Aldol reaction (dpeaa)DE-He213 Enamine (dpeaa)DE-He213 Transition state (dpeaa)DE-He213 Dual stereocontrol (dpeaa)DE-He213 Enantioselectivity (dpeaa)DE-He213
topic	misc Aldol reaction misc Enamine misc Transition state misc Dual stereocontrol misc Enantioselectivity
topic_unstemmed	misc Aldol reaction misc Enamine misc Transition state misc Dual stereocontrol misc Enantioselectivity
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title	New mechanistic approach in the enamine-based asymmetric organocatalysis
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title_full	New mechanistic approach in the enamine-based asymmetric organocatalysis
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author-letter	Gurka, András A.
doi_str_mv	10.1007/s11224-022-01952-w
title_sort	new mechanistic approach in the enamine-based asymmetric organocatalysis
title_auth	New mechanistic approach in the enamine-based asymmetric organocatalysis
abstract	Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule. © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022
abstractGer	Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule. © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022
abstract_unstemmed	Abstract During the course of my research in asymmetric organocatalysis, inversion of enantioselectivity was observed in the asymmetric aldol reactions of acetone with different aldehydes catalyzed by amphiphilic proline derivatives in aqueous media by varying only achiral components. It was not possible to explain the explored dual stereocontrol with the existing models, therefore I proposed a new mechanism for asymmetric aldol reactions catalyzed by l-amino acid derivatives in aqueous media and explained the explored phenomenon of inversion of enantioselectivity with different structures of micelle-stabilized transition state described as a metal-free version of the Zimmerman-Traxler model with explicit participation of a water molecule. Contrary to the existing models, according to the proposed mechanism, the formation of new bonds proceeds directly in the transition state stabilized by a water molecule, without the additional step of product iminium ion hydrolysis. The proposed mechanism has universal character, it is consistent with experimental results and general theoretical conceptions, and it is applicable to all enamine-based asymmetric organocatalytic reactions carried out not only in aqueous, but in organic media as well, because the initial step of catalytic cycle, which involves the formation of an enamine from the carbonyl compound and proline (derivative), liberates one water molecule. © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022
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title_short	New mechanistic approach in the enamine-based asymmetric organocatalysis
url	https://dx.doi.org/10.1007/s11224-022-01952-w
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doi_str	10.1007/s11224-022-01952-w
up_date	2024-07-03T23:31:18.212Z
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New mechanistic approach in the enamine-based asymmetric organocatalysis

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