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
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
收藏
页码:3277 / 3279
页数:3
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