ASYMMETRIC COPPER-CATALYZED CYCLOPROPANATION OF TRISUBSTITUTED AND UNSYMMETRICAL CIS-1,2-DISUBSTITUTED OLEFINS - MODIFIED BIS-OXAZOLINE LIGANDS

被引:309
作者
LOWENTHAL, RE [1 ]
MASAMUNE, S [1 ]
机构
[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(91)80110-R
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Cu(I) complexes of new bis-oxazolines (3-7) prepared from the corresponding amino alcohols and malono-bis-imidate exhibit high enantioselectivity of up to 94 %ee in the catalytic cyclopropanation of trisubstituted and unsymmetrical cis-1,2-disubstituted olefins. New diazoacetate reagents have also been developed giving high trans/cis ratios of up to 99:1 trans.
引用
收藏
页码:7373 / 7376
页数:4
相关论文
共 17 条
[2]  
ARATANI T, 1975, TETRAHEDRON LETT, P1707
[3]   ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION [J].
ARATANI, T ;
YONEYOSHI, Y ;
NAGASE, T .
TETRAHEDRON LETTERS, 1982, 23 (06) :685-688
[4]  
ARATANI T, 1977, TETRAHEDRON LETT, P2599
[5]  
Bolm C., 1991, ANGEW CHEM, V103, P556
[6]   CYCLOPROPANES FROM REACTIONS OF TRANSITION-METAL CARBENE COMPLEXES WITH OLEFINS [J].
BROOKHART, M ;
STUDABAKER, WB .
CHEMICAL REVIEWS, 1987, 87 (02) :411-432
[7]  
COREY EJ, 1991, J AM CHEM SOC, V113, P729
[8]   CARBENE COMPLEXES IN ORGANIC-SYNTHESIS [J].
DOTZ, KH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :587-608
[9]   CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP .
CHEMICAL REVIEWS, 1986, 86 (05) :919-939
[10]   EXCEPTIONALLY HIGH TRANS (ANTI) STEREOSELECTIVITY IN CATALYTIC CYCLOPROPANATION REACTIONS [J].
DOYLE, MP ;
BAGHERI, V ;
WANDLESS, TJ ;
HARN, NK ;
BRINKER, DA ;
EAGLE, CT ;
LOH, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :1906-1912