Selective Syntheses of 螖伪,尾 and 螖尾,纬 Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements

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• 作者：Xiaocong Xie ; Yi Li ; Joseph M. Fox
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：15
• 期：7
• 页码：1500-1503
• 全文大小：282K
• 年卷期：v.15,no.7(April 5, 2013)
• ISSN：1523-7052

文摘

Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to 螖^尾,纬 butenolides via a Claisen rearrangement or to the corresponding 螖^伪,尾 butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.