Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes
Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5)...
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E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
1993 |
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| Reproduktion: |
Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 |
|---|---|
| Übergeordnetes Werk: |
in: Tetrahedron Letters - Amsterdam : Elsevier, 34(1993), 28, Seite 4559-4562 |
| Übergeordnetes Werk: |
volume:34 ; year:1993 ; number:28 ; pages:4559-4562 |
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| 245 | 1 | 0 | |a Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes |
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| 520 | |a Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. | ||
| 520 | |a Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. | ||
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(DE-627)NLEJ176383778 (DE-599)GBVNLZ176383778 DE-627 ger DE-627 rakwb eng Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Curci, R. oth D'Accolti, L. oth Detomaso, A. oth Fusco, C. oth Takeuchi, K. oth Ohga, Y. oth Eaton, P.E. oth Chi Yip, Y. oth in Tetrahedron Letters Amsterdam : Elsevier 34(1993), 28, Seite 4559-4562 (DE-627)NLEJ175981779 (DE-600)2007074-3 0040-4039 nnns volume:34 year:1993 number:28 pages:4559-4562 http://linkinghub.elsevier.com/retrieve/pii/0040-4039(93)88085-W GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 34 1993 28 4559-4562 |
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(DE-627)NLEJ176383778 (DE-599)GBVNLZ176383778 DE-627 ger DE-627 rakwb eng Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Curci, R. oth D'Accolti, L. oth Detomaso, A. oth Fusco, C. oth Takeuchi, K. oth Ohga, Y. oth Eaton, P.E. oth Chi Yip, Y. oth in Tetrahedron Letters Amsterdam : Elsevier 34(1993), 28, Seite 4559-4562 (DE-627)NLEJ175981779 (DE-600)2007074-3 0040-4039 nnns volume:34 year:1993 number:28 pages:4559-4562 http://linkinghub.elsevier.com/retrieve/pii/0040-4039(93)88085-W GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 34 1993 28 4559-4562 |
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(DE-627)NLEJ176383778 (DE-599)GBVNLZ176383778 DE-627 ger DE-627 rakwb eng Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Curci, R. oth D'Accolti, L. oth Detomaso, A. oth Fusco, C. oth Takeuchi, K. oth Ohga, Y. oth Eaton, P.E. oth Chi Yip, Y. oth in Tetrahedron Letters Amsterdam : Elsevier 34(1993), 28, Seite 4559-4562 (DE-627)NLEJ175981779 (DE-600)2007074-3 0040-4039 nnns volume:34 year:1993 number:28 pages:4559-4562 http://linkinghub.elsevier.com/retrieve/pii/0040-4039(93)88085-W GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 34 1993 28 4559-4562 |
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(DE-627)NLEJ176383778 (DE-599)GBVNLZ176383778 DE-627 ger DE-627 rakwb eng Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Curci, R. oth D'Accolti, L. oth Detomaso, A. oth Fusco, C. oth Takeuchi, K. oth Ohga, Y. oth Eaton, P.E. oth Chi Yip, Y. oth in Tetrahedron Letters Amsterdam : Elsevier 34(1993), 28, Seite 4559-4562 (DE-627)NLEJ175981779 (DE-600)2007074-3 0040-4039 nnns volume:34 year:1993 number:28 pages:4559-4562 http://linkinghub.elsevier.com/retrieve/pii/0040-4039(93)88085-W GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 34 1993 28 4559-4562 |
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(DE-627)NLEJ176383778 (DE-599)GBVNLZ176383778 DE-627 ger DE-627 rakwb eng Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes 1993 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Curci, R. oth D'Accolti, L. oth Detomaso, A. oth Fusco, C. oth Takeuchi, K. oth Ohga, Y. oth Eaton, P.E. oth Chi Yip, Y. oth in Tetrahedron Letters Amsterdam : Elsevier 34(1993), 28, Seite 4559-4562 (DE-627)NLEJ175981779 (DE-600)2007074-3 0040-4039 nnns volume:34 year:1993 number:28 pages:4559-4562 http://linkinghub.elsevier.com/retrieve/pii/0040-4039(93)88085-W GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 34 1993 28 4559-4562 |
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selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes |
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Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes |
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Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. |
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Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. |
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Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration. Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b. |
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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">NLEJ176383778</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20210706022535.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">070505s1993 xx |||||o 00| ||eng c</controlfield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)NLEJ176383778</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)GBVNLZ176383778</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">Selective oxidation of tertiary-secondary vic-diols to α-hydroxy ketones by dioxiranes</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">1993</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">Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield > 97% with retention of configuration.</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Synthesis of α-ketols 7-11 in high yield upon oxidation of the corresponding vic-diols using 1a or 1b.</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">Curci, R.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">D'Accolti, L.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Detomaso, A.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Fusco, C.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Takeuchi, K.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Ohga, Y.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Eaton, P.E.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Chi Yip, Y.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">in</subfield><subfield code="t">Tetrahedron Letters</subfield><subfield code="d">Amsterdam : Elsevier</subfield><subfield code="g">34(1993), 28, Seite 4559-4562</subfield><subfield code="w">(DE-627)NLEJ175981779</subfield><subfield code="w">(DE-600)2007074-3</subfield><subfield code="x">0040-4039</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:34</subfield><subfield code="g">year:1993</subfield><subfield code="g">number:28</subfield><subfield code="g">pages:4559-4562</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">http://linkinghub.elsevier.com/retrieve/pii/0040-4039(93)88085-W</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">34</subfield><subfield code="j">1993</subfield><subfield code="e">28</subfield><subfield code="h">4559-4562</subfield></datafield></record></collection>
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7.399441 |