An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

Z Yang, X Chen, W Kong, S Xia, R Zheng…

Index: Yang, Zhaozhen; Chen, Xiaoyi; Kong, Wei; Xia, Siyuan; Zheng, Renwei; Luo, Fang; Zhu, Gangguo Organic and Biomolecular Chemistry, 2013 , vol. 11, # 13 p. 2175 - 2185

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Citation Number: 12

Abstract

An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio-and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chloro and (E)-α-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly ...

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