An Asymmetric Vinylogous Michael Cascade of Silyl Glyoximide, Vinyl Grignard, and Nitroalkenes via Long Range Stereoinduction

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• 作者：Gregory R. Boyce ; Jeffrey S. Johnson
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：81
• 期：4
• 页码：1712-1717
• 全文大小：363K
• ISSN：1520-6904

文摘

A diastereoselective auxiliary-mediated vinylation/[1,2]-Brook rearrangement/vinylogous Michael cascade of silyl glyoximide, vinylmagnesium bromide, and nitroalkenes is described. The reaction occurs with complete regio- and diastereocontrol in good yield. The diastereoselectivity is induced by a rare instance of 1,7-chirality transfer that is hypothesized to arise from a trans-multihetero-decalin transition state.