An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation

被引：138

作者：

Imada, Y ^{[1
]}

Iida, H

Murahashi, S

Naota, T

机构：

[1] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Toyonaka, Osaka 5608531, Japan

[2] Japan Sci & Technol Agcy JST, PRESTO, Toyonaka, Osaka 5608531, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 11期

关键词：

chemoselectivity; green chemistry; lactones; organocatalysis; oxidation;

D O I：

10.1002/anie.200462429

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Highly chemoselective Baeyer-Villiger oxidations can be performed in the presence of other reactive functionalities such as alcohols, olefins, and sulfides, which would undergo electrophilic oxidation under conventional conditions (see scheme). [DMRFlEt] +[ClO4]- (depicted blue) is a new class of flavin compound that catalyzes aerobic Baeyer-Villiger oxidations in the presence of Zn dust as the electron source. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1704 / 1706

页数：3

共 37 条

[1] Synthetic applications of nonmetal catalysts for homogeneous oxidations [J].

Adam, W ;

Saha-Möller, CR ;

Ganeshpure, PA .

CHEMICAL REVIEWS, 2001, 101 (11) :3499-3548

[2]

ALPHAND V, 1995, ENZYME CATALYSIS ORG, P745

[3]

[Anonymous], ANGEW CHEM

[4] Mild and efficient flavin-catalyzed H2O2 oxidation of tertiary amines to amine N-oxides [J].

Bergstad, K ;

Bäckvall, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6650-6655

[5] Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones [J].

Bolm, C ;

Beckmann, O ;

Palazzi, C .

CANADIAN JOURNAL OF CHEMISTRY, 2001, 79 (11) :1593-1597

[6]

Bolm C, 2000, CHIRALITY, V12, P523, DOI 10.1002/(SICI)1520-636X(2000)12:5/6<523::AID-CHIR39>3.3.CO

[7]

2-Q

[8]

Hudlicky M., 1990, OXIDATIONS ORGANIC C

[9] Flavin catalyzed oxidations of sulfides and amines with molecular oxygen [J].

Imada, Y ;

Iida, H ;

Ono, S ;

Murahashi, SI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2868-2869

[10]

Ishii Y., 2004, MODERN OXIDATION MET, P119

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