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

被引：308

作者：

LOWENTHAL, RE ^{[1
]}

MASAMUNE, S ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 50期

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

页码：7373 / 7376

页数：4

共 17 条

[1] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION
ARATANI, T
[J]. PURE AND APPLIED CHEMISTRY, 1985, 57 (12) : 1839 - 1844
[2] ARATANI T, 1975, TETRAHEDRON LETT, P1707
[3] ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION
ARATANI, T
YONEYOSHI, Y
NAGASE, T
[J]. 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
BROOKHART, M
STUDABAKER, WB
[J]. CHEMICAL REVIEWS, 1987, 87 (02) : 411 - 432
[7] COREY EJ, 1991, J AM CHEM SOC, V113, P729
[8] CARBENE COMPLEXES IN ORGANIC-SYNTHESIS
DOTZ, KH
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08): : 587 - 608
[9] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS
DOYLE, MP
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 919 - 939
[10] EXCEPTIONALLY HIGH TRANS (ANTI) STEREOSELECTIVITY IN CATALYTIC CYCLOPROPANATION REACTIONS
DOYLE, MP
BAGHERI, V
WANDLESS, TJ
HARN, NK
BRINKER, DA
EAGLE, CT
LOH, KL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) : 1906 - 1912

← 1 2 →