Highly selective catalyst-directed pathways to dihydropyrroles from vinyldiazoacetates and imines

被引:119
作者
Doyle, MP [1 ]
Yan, M [1 ]
Hu, WH [1 ]
Gronenberg, LS [1 ]
机构
[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
关键词
D O I
10.1021/ja029745q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Copper-catalyzed reactions of vinyldiazoacetates with imines occur via a pathway in which the activated imine undergoes electrophilic addition to the vinyldiazo compound, whereas reactions catalyzed by rhodium(II) proceed through a metal carbene to an intermediate iminium-ylide. Both pathways exhibit high stereoselectivities. Copyright © 2003 American Chemical Society.
引用
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页码:4692 / 4693
页数:2
相关论文
共 19 条
[1]   Catalytic asymmetric aziridination with a chiral VAPOL-boron Lewis acid [J].
Antilla, JC ;
Wulff, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :5099-5100
[2]  
Davies H. M. L., 2001, ORG REACTIONS, V57, P1
[3]   Stereoselective synthesis of epoxides by reaction of donor/acceptor-substituted carbenoids with α,β-unsaturated aldehydes [J].
Davies, HML ;
DeMeese, J .
TETRAHEDRON LETTERS, 2001, 42 (39) :6803-6805
[4]   Highly stereoselective syntheses of five- and seven-membered ring heterocycles from ylides generated by catalytic reactions of styryldiazoacetates with aldehydes and imines [J].
Doyle, MP ;
Hu, WH ;
Timmons, DJ .
ORGANIC LETTERS, 2001, 3 (23) :3741-3744
[5]   Epoxides and aziridines from diazoacetates via ylide intermediates [J].
Doyle, MP ;
Hu, WH ;
Timmons, DJ .
ORGANIC LETTERS, 2001, 3 (06) :933-935
[6]  
DOYLE MP, 1998, MODERN CATALYTIC MET, pCH2
[7]   Copper-amidophosphine catalyst in asymmetric addition of organozinc to imines [J].
Fujihara, H ;
Nagai, K ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :12055-12056
[8]   CARBENOID TRANSFER TO IMINES - A NEW ASYMMETRIC CATALYTIC SYNTHESIS OF AZIRIDINES [J].
HANSEN, KB ;
FINNEY, NS ;
JACOBSEN, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (06) :676-678
[9]  
Jorgensen KA, 2000, ANGEW CHEM INT EDIT, V39, P3558, DOI 10.1002/1521-3773(20001016)39:20<3558::AID-ANIE3558>3.0.CO
[10]  
2-I