New asymmetric synthesis of (-)-esermethole
A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction con...
Ausführliche Beschreibung
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| Autor*in: |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
1994 |
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| Reproduktion: |
Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 |
|---|---|
| Übergeordnetes Werk: |
in: Tetrahedron: Asymmetry - Amsterdam : Elsevier, 5(1994), 3, Seite 363-370 |
| Übergeordnetes Werk: |
volume:5 ; year:1994 ; number:3 ; pages:363-370 |
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NLEJ176498370 |
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| 245 | 1 | 0 | |a New asymmetric synthesis of (-)-esermethole |
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| 520 | |a A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. | ||
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| 700 | 1 | |a Villa, L. |4 oth | |
| 700 | 1 | |a Resta, I. |4 oth | |
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(DE-627)NLEJ176498370 (DE-599)GBVNLZ176498370 DE-627 ger DE-627 rakwb eng New asymmetric synthesis of (-)-esermethole 1994 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Pallavicini, M. oth Valoti, E. oth Villa, L. oth Resta, I. oth in Tetrahedron: Asymmetry Amsterdam : Elsevier 5(1994), 3, Seite 363-370 (DE-627)NLEJ176485422 (DE-600)2007143-7 0957-4166 nnns volume:5 year:1994 number:3 pages:363-370 http://linkinghub.elsevier.com/retrieve/pii/S0957-4166(00)86207-2 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 5 1994 3 363-370 |
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(DE-627)NLEJ176498370 (DE-599)GBVNLZ176498370 DE-627 ger DE-627 rakwb eng New asymmetric synthesis of (-)-esermethole 1994 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Pallavicini, M. oth Valoti, E. oth Villa, L. oth Resta, I. oth in Tetrahedron: Asymmetry Amsterdam : Elsevier 5(1994), 3, Seite 363-370 (DE-627)NLEJ176485422 (DE-600)2007143-7 0957-4166 nnns volume:5 year:1994 number:3 pages:363-370 http://linkinghub.elsevier.com/retrieve/pii/S0957-4166(00)86207-2 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 5 1994 3 363-370 |
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(DE-627)NLEJ176498370 (DE-599)GBVNLZ176498370 DE-627 ger DE-627 rakwb eng New asymmetric synthesis of (-)-esermethole 1994 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Pallavicini, M. oth Valoti, E. oth Villa, L. oth Resta, I. oth in Tetrahedron: Asymmetry Amsterdam : Elsevier 5(1994), 3, Seite 363-370 (DE-627)NLEJ176485422 (DE-600)2007143-7 0957-4166 nnns volume:5 year:1994 number:3 pages:363-370 http://linkinghub.elsevier.com/retrieve/pii/S0957-4166(00)86207-2 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 5 1994 3 363-370 |
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(DE-627)NLEJ176498370 (DE-599)GBVNLZ176498370 DE-627 ger DE-627 rakwb eng New asymmetric synthesis of (-)-esermethole 1994 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Pallavicini, M. oth Valoti, E. oth Villa, L. oth Resta, I. oth in Tetrahedron: Asymmetry Amsterdam : Elsevier 5(1994), 3, Seite 363-370 (DE-627)NLEJ176485422 (DE-600)2007143-7 0957-4166 nnns volume:5 year:1994 number:3 pages:363-370 http://linkinghub.elsevier.com/retrieve/pii/S0957-4166(00)86207-2 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 5 1994 3 363-370 |
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(DE-627)NLEJ176498370 (DE-599)GBVNLZ176498370 DE-627 ger DE-627 rakwb eng New asymmetric synthesis of (-)-esermethole 1994 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Pallavicini, M. oth Valoti, E. oth Villa, L. oth Resta, I. oth in Tetrahedron: Asymmetry Amsterdam : Elsevier 5(1994), 3, Seite 363-370 (DE-627)NLEJ176485422 (DE-600)2007143-7 0957-4166 nnns volume:5 year:1994 number:3 pages:363-370 http://linkinghub.elsevier.com/retrieve/pii/S0957-4166(00)86207-2 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 5 1994 3 363-370 |
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A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. |
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A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. |
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A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps. |
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<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">NLEJ176498370</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20210706024218.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">070505s1994 xx |||||o 00| ||eng c</controlfield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)NLEJ176498370</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)GBVNLZ176498370</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">New asymmetric synthesis of (-)-esermethole</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">1994</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">z</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zu</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10^oC, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilaceta mide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps.</subfield></datafield><datafield tag="533" ind1=" " ind2=" "><subfield code="f">Elsevier Journal Backfiles on ScienceDirect 1907 - 2002</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Pallavicini, M.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Valoti, E.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Villa, L.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Resta, I.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">in</subfield><subfield code="t">Tetrahedron: Asymmetry</subfield><subfield code="d">Amsterdam : Elsevier</subfield><subfield code="g">5(1994), 3, Seite 363-370</subfield><subfield code="w">(DE-627)NLEJ176485422</subfield><subfield code="w">(DE-600)2007143-7</subfield><subfield code="x">0957-4166</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:5</subfield><subfield code="g">year:1994</subfield><subfield code="g">number:3</subfield><subfield code="g">pages:363-370</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">http://linkinghub.elsevier.com/retrieve/pii/S0957-4166(00)86207-2</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_H</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">ZDB-1-SDJ</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_NL_ARTICLE</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">5</subfield><subfield code="j">1994</subfield><subfield code="e">3</subfield><subfield code="h">363-370</subfield></datafield></record></collection>
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