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

被引：116

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 16期

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

页码：4692 / 4693

页数：2

共 19 条

[1] Catalytic asymmetric aziridination with a chiral VAPOL-boron Lewis acid
Antilla, JC
Wulff, WD
[J]. 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
Davies, HML
DeMeese, J
[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
Doyle, MP
Hu, WH
Timmons, DJ
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3741 - 3744
[5] Epoxides and aziridines from diazoacetates via ylide intermediates
Doyle, MP
Hu, WH
Timmons, DJ
[J]. 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
Fujihara, H
Nagai, K
Tomioka, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 12055 - 12056
[8] CARBENOID TRANSFER TO IMINES - A NEW ASYMMETRIC CATALYTIC SYNTHESIS OF AZIRIDINES
HANSEN, KB
FINNEY, NS
JACOBSEN, EN
[J]. 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

← 1 2 →