One-Pot (1-Ethoxycarbonylcyclopropyl)triphenylphosphonium Tetrafluoroborate Ring-Opening and Wittig Reaction
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- 作者：Seung Won Chung ; Mark S. Plummer ; Laura A. McAllister ; Robert M. Oliver ; III ; Joseph A. Abramite ; Yue Shen ; Jianmin Sun ; Daniel P. Uccello ; Joel T. Arcari ; Loren M. Price ; Justin I. Montgomery
- 刊名：Organic Letters
- 出版年：2011
- 出版时间：October 7, 2011
- 年：2011
- 卷：13
- 期：19
- 页码：5338-5341
- 全文大小：708K
- 年卷期：v.13,no.19(October 7, 2011)
- ISSN：1523-7052
文摘
An efficient method was developed for the synthesis of 2-methylene-4-substituted ethyl butyrates via cyclopropyl opening followed by a Wittig reaction. The desired products were formed in a two-step, one-pot reaction sequence. Alternatively, the key intermediate ylide 2 was isolable and could be stored under oxygen-free conditions and subsequently utilized. A variety of nucleophiles were found to open the commercially available cyclopropane 1. The resulting ylide reacted with aldehydes to provide E-olefinic products.