(Z)-selective Wittig and Corey-Chaykovsky reactions of propargyl ylides using trialkylgallium bases

作者：Nishimura Yoshio; Shiraishi Takao; Yamaguchi Masahiko^*

来源：Tetrahedron Letters, 2008, 49(21): 3492-3495.

DOI：10.1016/j.tetlet.2008.03.086

Trialkylgalliums deprotonated propargylphosphonium salts and propargylsulfonium salts to form propargyl ylides. The resulted organogallium intermediates underwent the Wittig reaction and the Corey-Chaykovsky reaction with aldehydes giving (Z)-enynes and (Z)-epoxides predominantly. The use of an appropriate trialkylgallium is essential for the stereoselectivity.

• 出版日期2008-5-19