Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles

被引：169

作者：

Chuprakov, Stepan ^{[1
]}

Gevorgyan, Vladimir ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 22期

关键词：

D O I：

10.1021/ol702084f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly efficient regiodivergent method for the synthesis of N-fused heterocycles via transition-metal-catalyzed rearrangement of 3-iminocyclopropenes has been developed.

引用

页码：4463 / 4466

页数：4

共 39 条

[1] Strain energy of small ring hydrocarbons. Influence of C-H bond dissociation energies
Bach, RD
Dmitrenko, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) : 4444 - 4452
[2] BEHNISCH R, 1994, HOUBEN WEYL, V6, P3223
[3] PRACTICAL ORGANIC-SYNTHESIS WITH STRAINED-RING MOLECULES - RHODIUM-CATALYZED CARBONYLATION OF CYCLOPROPENYL ESTERS AND CYCLOPROPENYL KETONES TO ALPHA-PYRONES AND OF VINYL CYCLOPROPENES TO PHENOLS
CHO, SH
LIEBESKIND, LS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) : 2631 - 2634
[4] Direct palladium-catalyzed arylation of cyclopropenes
Chuprakov, S
Rubin, M
Gevorgyan, V
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3714 - 3715
[5] Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles
Chuprakov, Stepan
Hwang, Frank W.
Gevorgyan, Vladimir
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) : 4757 - 4759
[6] DIRECT SYNTHESIS OF FURANS BY 3+2 CYCLO-ADDITIONS BETWEEN RHODIUM(II) ACETATE STABILIZED CARBENOIDS AND ACETYLENES
DAVIES, HML
ROMINES, KR
[J]. TETRAHEDRON, 1988, 44 (11) : 3343 - 3348
[7] Dirhodium(II) tetra(N-(dodecyl benzenesulfonyl)prolinate) catalyzed enantioselective cyclopropenation of alkynes
Davies, HML
Lee, GH
[J]. ORGANIC LETTERS, 2004, 6 (08) : 1233 - 1236
[8] Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates
Davies, HML
Townsend, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) : 6595 - 6603
[9] Cyclopropenes in the 1,3-dipolar cycloaddition with carbonyl ylides:: Experimental and theoretical evidence for the enhancement of σ-withdrawal in 3-substituted-cyclopropenes
Diev, Vyacheslav V.
Kostikov, Rafael R.
Gleiter, Rolf
Molchanov, Alexander P.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) : 4066 - 4077
[10] Metal mediated and catalyzed nucleophilic additions to cyclopropenes
Fox, JM
Yan, N
[J]. CURRENT ORGANIC CHEMISTRY, 2005, 9 (07) : 719 - 732

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