One-Pot (1-Ethoxycarbonylcyclopropyl)triphenylphosphonium Tetrafluoroborate Ring-Opening and Wittig Reaction
Organic Letters2011Vol. 13(19), pp. 5338–5341
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Seung Won Chung, Mark S. Plummer, Laura A. McAllister, Robert M. Oliver, J. A. Abramite, Yue Shen, Jianmin Sun, Daniel P. Uccello, Joel T. Arcari, Loren Price, Justin I. Montgomery
Abstract
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.
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