(Z)-Selective Wittig and Corey–Chaykovsky reactions of propargyl ylides using trialkylgallium bases
                                
                                    
                                        作者:Yoshio Nishimura、Takao Shiraishi、Masahiko Yamaguchi                                    
                                    
                                        DOI:10.1016/j.tetlet.2008.03.086
                                    
                                    
                                        日期:2008.5
                                    
                                    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. (c) 2008 Elsevier Ltd. All rights reserved.