TMG catalyzed cyclopropanation of cyclopentenone. Illustration by a simple synthesis of bicyclo[3.1.0]hexane-2-one derivatives

被引：12

作者：

Zhang, Fuyao ^{[1
]}

Moher, Eric D. ^{[1
]}

Zhang, Tony Y. ^{[1
]}

机构：

[1] Eli Lilly & Co, Lilly Corp Ctr, Lilly Res Labs, Chem Prod R&D, Indianapolis, IN 46285 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 18期

关键词：

D O I：

10.1016/j.tetlet.2007.03.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic preparation of bicyclo[3.1.0]hexane-2-one-6-carboxylic acid ethyl ester 1 is described by cyclopropanation of cyclopentenone using 1,1,3,3-tetramethylguanidine (TMG) as a catalyst in high yield and high diastereoselectivity. This process has been applied to an efficient synthesis of the important intermediate, beta-hydroxyl cyclopentanone 2. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3277 / 3279

页数：3

共 15 条

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[3] Silver(I)-Catalyzed Oxidative Cyclopropanation of 1,6-Enynes: Synthesis of 3-Aza-bicyclo[3.1.0]hexane Derivatives
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[4] Addition of diazoalkanes to enynes promoted by a ruthenium catalyst:: Simple synthesis of alkenyl bicyclo[3.1.0]hexane derivatives
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[6] DISSYMMETRIC CHROMOPHORES .2. CIRCULAR-DICHROISM OF (2R)-BICYCLO[3.1.0]HEXAN-2-ONE AND (2S)-6,6-DIMETHYLBICYCLO[3.1.0]HEXANE-2-ONE
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