ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX

被引:112
作者
AOKI, S [1 ]
MIKAMI, K [1 ]
TERADA, M [1 ]
NAKAI, T [1 ]
机构
[1] TOKYO INST TECHNOL,DEPT CHEM TECHNOL,MEGURO KU,TOKYO 152,JAPAN
关键词
ASYMMETRIC CATALYSIS; ENANTIOCONTROL; DIASTEREOCONTROL; ALLYLIC SILANE; ALLYLIC STANNANE; CARBONYLADDITION REACTION; CARBONYL-ENE REACTION; GLYOXYLATE; BINAPHTHOL-DERIVED TITANIUM DIHALIDE; CHIRAL TITANIUM COMPLEX;
D O I
10.1016/S0040-4020(01)80535-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral titanium complex (1), prepared in situ from optically pure binaphthol and diisopropoxytitanium dihalide in the presence of molecular sieves, is shown to catalyze the addition reactions of crotylsilanes and -stannanes to glyoxylates to afford (syn)-alpha-hydroxy-beta-methyl esters in highly scalemic forms with high diastereoselectivity.
引用
收藏
页码:1783 / 1792
页数:10
相关论文
共 44 条
[1]  
Bosnich B., 1986, ASYMMETRIC CATALYSIS
[2]   STEREOCHEMISTRY OF ALLYLMETAL ALDEHYDE CONDENSATIONS .2. ALLYLSTANNANES [J].
DENMARK, SE ;
WEBER, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) :7970-7971
[3]   ON THE STEREOCHEMISTRY OF ALLYLMETAL-ALDEHYDE CONDENSATIONS [J].
DENMARK, SE ;
WEBER, EJ .
HELVETICA CHIMICA ACTA, 1983, 66 (06) :1655-1660
[4]  
DOYLE TW, 1980, ANTICANCER AGENTS BA, pCH2
[5]  
Fleming I., 1989, ORG REACTIONS, V37, P57
[6]  
FLEMING I, 1991, CHEMTRACTS ORGANIC C, V4, P21
[7]  
FURUTA K, 1991, SYNLETT, P561
[8]  
HANESSIAN S, 1983, TOTAL SYNTHESIS NATU, P132
[9]   CHIRAL LEWIS ACID IN CATALYTIC ASYMMETRIC REACTIONS [J].
HAYASHI, Y ;
NARASAKA, K .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1990, 48 (04) :280-290
[10]   STEREOSELECTIVE SYNTHESES OF BUILDING-BLOCKS WITH 3 CONSECUTIVE STEREOGENIC CENTERS - IMPORTANT PRECURSORS OF POLYKETIDE NATURAL-PRODUCTS [J].
HOFFMANN, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (06) :489-503