Stereoselective cyclopropanation with a sultam carbenoid

被引:22
作者
Haddad, N
Galili, N
机构
[1] Department of Chemistry, Technion-Israel Inst. of Technology
基金
以色列科学基金会;
关键词
D O I
10.1016/S0957-4166(97)00463-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Stereoselective cyclopropanation of alkenes with the Oppolzer's sultam carbenoid was examined for the first time. The addition reaction proceeds in high yields on substituted alkenes and provides an easy access for stereoselective preparation of di-and tri-substituted cyclopropanes. The synthetic utility of the title reaction was demonstrated in the stereoselective preparation of 1. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3367 / 3370
页数:4
相关论文
共 19 条
[1]  
[Anonymous], COMPLETE WORKS
[2]   EXPERIMENTAL-EVIDENCE FOR THE TWISTED APPROACH IN INTRAMOLECULAR 2+2 PHOTOCYCLOADDITIONS [J].
BECKER, D ;
MORLENDER, N ;
HADDAD, N .
TETRAHEDRON LETTERS, 1995, 36 (11) :1921-1924
[3]   Highly efficient trapping of short-lived 1,4-diradicals, the order of first bond formation in the intramolecular photocycloaddition of 3-(4'-pentenyl)-cyclohex-2-enones. [J].
Becker, D ;
Galili, N ;
Haddad, N .
TETRAHEDRON LETTERS, 1996, 37 (49) :8941-8944
[4]   EFFICIENT SYNTHESIS AND INTRAMOLECULAR CYCLOPROPANATION OF UNSATURATED DIAZOACETIC ESTERS [J].
COREY, EJ ;
MYERS, AG .
TETRAHEDRON LETTERS, 1984, 25 (33) :3559-3562
[5]   CHIRAL RHODIUM(II) CARBOXAMIDES - A NEW CLASS OF CATALYSTS FOR ENANTIOSELECTIVE CYCLOPROPANATION REACTIONS [J].
DOYLE, MP ;
BRANDES, BD ;
KAZALA, AP ;
PIETERS, RJ ;
JARSTFER, MB ;
WATKINS, LM ;
EAGLE, CT .
TETRAHEDRON LETTERS, 1990, 31 (46) :6613-6616
[6]   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
[7]  
DOYLE MP, 1993, SYNLETT, P151
[8]  
DOYLE MP, 1995, COMPREHENSIVE ORGA 2, V12
[9]   The order of first bond formation in the intramolecular photocycloaddition of 2-(4'-pentenyl)-cyclohex-2-enones [J].
Haddad, N ;
Galili, N .
TETRAHEDRON LETTERS, 1997, 38 (34) :6083-6086
[10]   Cyclopropanation of unsaturated sugars with ethyl diazoacetate [J].
Hoberg, JO ;
Claffey, DJ .
TETRAHEDRON LETTERS, 1996, 37 (15) :2533-2536