Rhodium-Catalyzed Cycloisomerization Involving Cyclopropenes: Efficient Stereoselective Synthesis of Medium-Sized Heterocyclic Scaffolds

被引：100

作者：

Miege, Frederic ^{[1
]}

Meyer, Christophe ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI ParisTech, CNRS, Lab Chim Organ, UMR 7084, F-75231 Paris 05, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 26期

关键词：

carbenoids; cyclopropanation; diastereoselectivity; homogeneous catalysis; rhodium; ALPHA-DIAZO KETONES; METAL CARBENE TRANSFORMATIONS; ALKYNE INSERTION REACTIONS; GOLD(I)-CATALYZED CYCLOISOMERIZATION; INTRAMOLECULAR CYCLOPROPANATION; ORGANIC-SYNTHESIS; CYCLIZATION REACTIONS; GOLD CATALYSIS; ALKYLIDENECYCLOPROPANE DERIVATIVES; ASYMMETRIC CYCLOPROPANATION;

D O I：

10.1002/anie.201101220

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A happy medium: The title reaction of cyclopropenyl carbinols and carbinylamines gives carbo- and heterocycles with a [6.1.0] bicyclic ring fused to an aromatic ring (see scheme, Alloc=allyloxycarbonyl, Boc=tert- butyloxycarbonyl). These reactions are the first examples of the formation of medium-sized rings by the intramolecular cyclopropanation of an alkene with a donor-substituted rhodium carbenoid, which is not generated from a diazo compound. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5932 / 5937

页数：6

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