Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with N-Sulfonyl 1,2,3-Triazoles

被引：253

作者：

Chuprakov, Stepan ^{[1
]}

Kwok, Sen Wai ^{[1
]}

Zhang, Li ^{[1
]}

Lercher, Lukas ^{[1
]}

Fokin, Valery V. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 50期

基金：

美国国家卫生研究院;

关键词：

C-H INSERTION; ASYMMETRIC CYCLOPROPANATION; DIRHODIUM(II); ALKENES; TRANSANNULATION; ENHANCEMENT; SELECTIVITY; CARBENOIDS; ACTIVATION; NITRILES;

D O I：

10.1021/ja908075u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Sulfonyl 1,2,3-triazoles readily form rhodium(II) azavinyl carbenes, which react with olefins to produce cyclopropanes with excellent diastereo- and enantioselectivity and in high yield.

引用

页码：18034 / +

页数：3

共 29 条

[1] Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides [J].

Cassidy, Michael P. ;

Raushel, Jessica ;

Fokin, Valery V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3154-3157

[2] Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles [J].

Chuprakov, Stepan ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2007, 9 (22) :4463-4466

[3] Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles [J].

Chuprakov, Stepan ;

Hwang, Frank W. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4757-4759

[4] Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen [J].

Davies, HML ;

Nagashima, T ;

Klino, JL .

ORGANIC LETTERS, 2000, 2 (06) :823-826

[5] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].

Davies, HML ;

Beckwith, REJ .

CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903

[6] Dirhodium(II) tetra(N-(dodecyl benzenesulfonyl)prolinate) catalyzed enantioselective cyclopropenation of alkynes [J].

Davies, HML ;

Lee, GH .

ORGANIC LETTERS, 2004, 6 (08) :1233-1236

[7] Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates [J].

Davies, HML ;

Townsend, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6595-6603

[8] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].

Davies, Huw M. L. ;

Manning, James R. .

NATURE, 2008, 451 (7177) :417-424

[9] Balance between allylic C-H activation and cyclopropanation in the reactions of donor/acceptor-substituted rhodium carbenoids with trans-alkenes [J].

Davies, Huw M. L. ;

Coleman, Michael G. ;

Ventura, Dominic L. .

ORGANIC LETTERS, 2007, 9 (24) :4971-4974

[10] Chiral Crown Conformation of Rh2(S-PTTL)4: Enantioselective Cyclopropa nation with α-Alkyl-α-diazoesters [J].

DeAngelis, Andrew ;

Dmitrenko, Olga ;

Yap, Glenn P. A. ;

Fox, Joseph M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (21) :7230-+

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