Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols in Water

被引：43

作者：

Malkov, Andrei V. ^{[1
]}

Czemerys, Louise ^{[1
]}

Malyshev, Denis A. ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 09期

基金：

英国工程与自然科学研究理事会;

关键词：

AQUEOUS HYDROGEN-PEROXIDE; CHIRAL HYDROXAMIC ACIDS; ENANTIOSELECTIVE EPOXIDATIONS; LIGANDS; OXIDATIONS; COMPLEX; OLEFINS; ALKENES; DESIGN;

D O I：

10.1021/jo900294h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric V-catalyzed epoxidation of allylic alcohols can be carried out in water with chiral ligands, which incorporate sulfonamide and hydroxamic acid fragments. Furthermore, the reaction, notorious for its ligand-deceleration effect, in water turned into the ligand-accelerated process. By using this aqueous protocol, a range of allylic alcohols were epoxidized with up to 94% ee.

引用

页码：3350 / 3355

页数：6

共 50 条

[21] Design of optically active hydroxamic acids as ligands in vanadium-catalyzed asymmetric epoxidation
1653, Chemical Soc of Japan, Tokyo, Japan (73):
[22] Design of optically active hydroxamic acids as ligands in vanadium-catalyzed asymmetric epoxidation
Hoshino, Y
Murase, N
Oishi, M
Yamamoto, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (07) : 1653 - 1658
[23] VANADIUM-CATALYZED EPOXIDATIONS .1. NEW SELECTIVITY PATTERN FOR ACYCLIC ALLYLIC ALCOHOLS
MIHELICH, ED
TETRAHEDRON LETTERS, 1979, (49) : 4729 - 4732
[24] Mild and Selective Vanadium-Catalyzed Oxidation of Benzylic, Allylic, and Propargylic Alcohols Using Air
Hanson, Susan K.
Wu, Ruilian
Silks, L. A. Pete
ORGANIC LETTERS, 2011, 13 (08) : 1908 - 1911
[25] Nb(salan)-catalyzed asymmetric epoxidation of allylic alcohols with hydrogen peroxide
Egami, Hiromichi
Katsuki, Tsutomu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (28) : 5171 - 5174
[26] CHIRAL HYDROXAMIC ACIDS AS LIGANDS IN VANADIUM CATALYZED ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS BY TERT-BUTYL HYDROPEROXIDE
MICHAELSON, RC
PALERMO, RE
SHARPLESS, KB
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) : 1990 - 1992
[27] Asymmetric epoxidation of chiral allylic alcohols
Warmerdam, EGJC
vandenNieuwendijk, AMCH
Brussee, J
Kruse, CG
vanderGen, A
TETRAHEDRON-ASYMMETRY, 1996, 7 (09) : 2539 - 2550
[28] ASYMMETRIC EPOXIDATION OF FLUORINATED ALLYLIC ALCOHOLS
GOSMINI, C
DUBUFFET, T
SAUVETRE, R
NORMANT, JF
TETRAHEDRON-ASYMMETRY, 1991, 2 (03) : 223 - 230
[29] Asymmetric epoxidation of chiral allylic alcohols
Tetrahedron Asymmetry, 9 (2539):
[30] Vanadium-catalyzed asymmetric cyanohydrin synthesis
Belokon, YN
North, M
Parsons, T
ORGANIC LETTERS, 2000, 2 (11) : 1617 - 1619

← 1 2 3 4 5 →