OPTICALLY-ACTIVE LACTONES FROM A BAEYER-VILLIGER-TYPE METAL-CATALYZED OXIDATION WITH MOLECULAR-OXYGEN

被引：201

作者：

BOLM, C ^{[1
]}

SCHLINGLOFF, G ^{[1
]}

WEICKHARDT, K ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 18期

关键词：

D O I：

10.1002/anie.199418481

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Simple, mild, and enantioselective! Oxygen reacts with ketone 1 in the presence of pivalaldehyde (R  tBu) and a chiral copper complex (cat.*) to give lactone 2 in 47% yield and 69% ee. Other enantioselective Baeyer—Villiger‐type oxidations had previously only been achieved with the help of enzymes. (Figure Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany

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页码：1848 / 1849

页数：2

相关论文

共 31 条

[21] AEROBIC OXIDATIONS OF ALKANES AND ALKENES IN THE PRESENCE OF ALDEHYDES CATALYZED BY COPPER-SALTS [J].

MURAHASHI, SI ;

ODA, Y ;

NAOTA, T ;

KOMIYA, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :139-140

[22]

Ojima I., 2010, CATALYTIC ASYMMETRIC

[23] MICROBIOLOGICAL TRANSFORMATIONS .25. ENANTIOSELECTIVE BAEYER-VILLIGER OXIDATION AS A TOOL FOR THE SYNTHESIS OF ENANTIOPURE BICYCLIC FUROFURAN AND PYROFURAN CHIRONS [J].

PETIT, F ;

FURSTOSS, R .

TETRAHEDRON-ASYMMETRY, 1993, 4 (06) :1341-1352

[24] CHIRAL SEMICORRINS AND RELATED NITROGEN-HETEROCYCLES AS LIGANDS IN ASYMMETRIC CATALYSIS [J].

PFALTZ, A .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (06) :339-345

[25] MECHANISM OF COPPER-CATALYZED OXYGENATION OF KETONES [J].

SAYRE, LM ;

JIN, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (19) :3498-3503

[26] THE ENZYMATIC BAEYER-VILLIGER OXIDATION OF A SERIES OF BICYCLO[2.2.1]HEPT-2-EN-7-ONES [J].

TASCHNER, MJ ;

PEDDADA, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (19) :1384-1385

[27] ENZYMIC BAEYER-VILLIGER OXIDATIONS BY FLAVIN-DEPENDENT MONOOXYGENASES [J].

WALSH, CT ;

CHEN, YCJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (03) :333-343

[28]

WALSH CT, 1988, ANGEW CHEM, V100, P342

[29] ENANTIOSELECTIVE EPOXIDATION OF UNFUNCTIONALIZED OLEFINS WITH MOLECULAR-OXYGEN AND ALDEHYDE CATALYZED BY OPTICALLY-ACTIVE MANGANESE(III) COMPLEXES [J].

YAMADA, T ;

IMAGAWA, K ;

NAGATA, T ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1992, (11) :2231-2234

[30] THE BAEYER-VILLIGER OXIDATION OF KETONES CATALYZED BY NICKEL(II) COMPLEXES WITH COMBINED USE OF MOLECULAR-OXYGEN AND ALDEHYDE [J].

YAMADA, T ;

TAKAHASHI, K ;

KATO, K ;

TAKAI, T ;

INOKI, S ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1991, (04) :641-644

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