The diastereoselective epoxidation of olefins in supercritical carbon dioxide.

被引:26
作者
Haas, GR [1 ]
Kolis, JW [1 ]
机构
[1] Clemson Univ, Dept Chem, Clemson, SC 29634 USA
关键词
D O I
10.1016/S0040-4039(98)01212-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylic alcohols are epoxidized with tert-butyl hydroperoxide in the presence of a vanadyl salen ore-transfer catalyst in supercritical CO2 The metal catalyst was prepared in a simple two.step, Schiff base reaction to form the salen ligand, followed by complexation to the vanadyl group. The epoxidation reactions are clean and give both high yields and good diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5923 / 5926
页数:4
相关论文
共 18 条
[11]  
OJIMA I, 1993, CATALYTIC ASYMMETRIC, P160
[12]   MECHANISM OF THE CHROMIUM-CATALYZED EPOXIDATION OF OLEFINS - ROLE OF OXOCHROMIUM(V) CATIONS [J].
SAMSEL, EG ;
SRINIVASAN, K ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7606-7617
[13]  
Sharpless K.B., 1979, ALDRICHIM ACTA, V12, P63
[14]   EPOXIDATION OF OLEFINS WITH CATIONIC (SALEN)MNIII COMPLEXES - THE MODULATION OF CATALYTIC ACTIVITY BY SUBSTITUENTS [J].
SRINIVASAN, K ;
MICHAUD, P ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2309-2320
[15]   DUAL PATHWAYS FOR MANGANESE CATALYSIS OF OLEFIN OXIDATION WITH ALKYL HYDROPEROXIDES [J].
SRINIVASAN, K ;
PERRIER, S ;
KOCHI, JK .
JOURNAL OF MOLECULAR CATALYSIS, 1986, 36 (03) :297-317
[16]   STEREOSELECTIVE EPOXIDATIONS OF ACYCLIC ALLYLIC ALCOHOLS BY TRANSITION METAL-HYDROPEROXIDE REAGENTS - SYNTHESIS OF DL-C18 CECROPIA JUVENILE-HORMONE FROM FARNESOL [J].
TANAKA, S ;
YAMAMOTO, H ;
NOZAKI, H ;
SHARPLES.KB ;
MICHAELS.RC ;
CUTTING, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (16) :5254-5255
[17]   CATALYSIS OF ALKENE OXIDATION BY NICKEL SALEN COMPLEXES USING NAOCL UNDER PHASE-TRANSFER CONDITIONS [J].
YOON, H ;
BURROWS, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :4087-4089
[18]   ASYMMETRIC OLEFIN EPOXIDATION WITH SODIUM-HYPOCHLORITE CATALYZED BY EASILY PREPARED CHIRAL MN(III) SALEN COMPLEXES [J].
ZHANG, W ;
JACOBSEN, EN .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2296-2298