Addition of diazoalkanes to enynes promoted by a ruthenium catalyst:: Simple synthesis of alkenyl bicyclo[3.1.0]hexane derivatives

被引：72

作者：

Monnier, F

Castillo, D

Dérien, S

Toupet, L

Dixneuf, PH

机构：

[1] Univ Rennes 1, UMR 6509 CNRS, Inst Chim Rennes, F-35042 Rennes, France

[2] Univ Rennes 1, UMR 6626 CNRS, Grp Mat Condensee & Mat, F-35042 Rennes, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 44期

关键词：

cyclization; diazo compounds; enynes; heterocycles; ruthenium;

D O I：

10.1002/anie.200352477

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[C*pRuCl(cod)] (C*p=C5Me 5, cod=cyclooctadiene) promotes the reaction of 1,6-enynes with an excess of diazoalkane in dioxane in one step to afford selectively 1-alkenyl bicyclo[3.1.0]hexane derivatives (see scheme, X=O, NTs; Y=CO2Et; R1=H, Me; R2=H; Ts=p-toluenesulfonyl). This novel reaction involves the stereoselective formation of three C-C bonds and a cyclopropanation step.

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收藏

页码：5474 / 5477

页数：4

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