TRIDENTATE BETA-HYDROPEROXY ALCOHOLS AS NOVEL OXYGEN DONORS FOR THE TITANIUM-CATALYZED EPOXIDATION OF GAMMA,DELTA-UNSATURATED ALPHA,BETA-DIOLS - A DIRECT DIASTEREOSELECTIVE SYNTHESIS OF EPOXY DIOLS

被引:19
作者
ADAM, W [1 ]
PETERS, K [1 ]
RENZ, M [1 ]
机构
[1] MAX PLANCK INST FESTKORPERFORSCH,STUTTGART,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 10期
关键词
D O I
10.1002/anie.199411071
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An attractive direct route to epoxy diols 2 relies on the Ti‐catalyzed epoxidation of enediols 1 with 2‐hydroperoxy‐2‐phenylpropan‐l‐ol. Under conventional Sharpless epoxidation conditions (bidentate tBuOOH) diols 1 react very sluggishly; however, with the new tridentate oxygen donor these same diols undergo smooth reaction to give products 2 in high diastereoselectivity and without the use of protecting groups. (Figure Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
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页码:1107 / 1108
页数:2
相关论文
共 17 条
[11]  
Masamune S., 1982, ALDRICHIM ACTA, V15, P47
[12]  
MORRISON JD, 1985, ASYMMETRIC SYNTHESIS, V5
[13]   RATES AND SCOPE OF OXIDATIVE CARBON-CARBON CLEAVAGE OF EPOXIDES BY ALKALINE HYDROGEN-PEROXIDE [J].
OGATA, Y ;
SAWAKI, Y ;
SHIMIZU, H .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) :1760-1763
[14]  
ROSSITER BE, 1985, ASYMMETRIC SYNTHESIS, P216
[15]  
TAKANO S, 1991, SYNLETT, P548
[16]   INVERSION OF ENANTIOSELECTIVITY IN THE KINETIC RESOLUTION MODE OF THE KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION REACTION [J].
TAKANO, S ;
IWABUCHI, Y ;
OGASAWARA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2786-2787
[17]   MECHANISM OF ASYMMETRIC EPOXIDATION .1. KINETICS [J].
WOODARD, SS ;
FINN, MG ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :106-113