DABCO-catalyzed 1, 4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene

W Zhang, H Xu, H Xu, W Tang

Index: Zhang, Wen; Xu, Huadong; Xu, Hui; Tang, Weiping Journal of the American Chemical Society, 2009 , vol. 131, p. 3832 - 3833

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Citation Number: 69

Abstract

A DABCO-catalyzed highly regio-and stereoselective syn-1, 4-bromolactonization of conjugated enynes was discovered. The 1, 4-addition occurred selectively over 1, 2-addition for most enynes. In contrast to anti 1, 2-addition to alkenes, where two adjacent stereogenic centers are created, 1, 4-addition across conjugated enynes can produce a stereogenic center and an axially chiral allene simultaneously. Enynes with Z and E configurations ...