Facile synthesis of α-difluoromethyl α-propargylamines from CF_2H-substituted N-tert-butanesulfinyl ketimines  

作　　者：Hui Chen Wei Yu Xin Hua Guo Wei Dong Meng Yan Gen Huang 

机构地区：[1]College of Chemistry,Chemical Engineering and Biotechnology,Donghua University,Shanghai 201620,China

出　　处：《Chinese Chemical Letters》2012年第3期277-280,共4页中国化学快报（英文版）

基　　金：The Shanghai Pujiang Program(No09PJ1400800);the Fundamental Research Funds for the Central Universities and the Scientific Research Foundation for the Returned Overseas Chinese Scholars,State Education Ministry

摘　　要：Stereoselective approach for preparation ofα-difluoromethylα-propargylamines has been developed.1,2-Addition of lithium acetylides to diverse chiral difluoromethylated（S）-N-tert-butanesulfinyl ketimines by using Ti（O^iPr）_4 as catalyst and THF as solvent afforded N-tert-butanesulfinamides in good to excellent yields（51-93%） and good diastereoselectivities（dr.85：15 to 93：7）.The N-tert -butanesulfinyl group can be readily cleaved under mild acidic condition（4 mol/L HCl in dioxane） to provide the correspondingα-difiuoromethylα-propargylamine in excellent yields（90-95%）.Stereoselective approach for preparation ofα-difluoromethylα-propargylamines has been developed.1,2-Addition of lithium acetylides to diverse chiral difluoromethylated（S）-N-tert-butanesulfinyl ketimines by using Ti（O^iPr）_4 as catalyst and THF as solvent afforded N-tert-butanesulfinamides in good to excellent yields（51-93%） and good diastereoselectivities（dr.85：15 to 93：7）.The N-tert -butanesulfinyl group can be readily cleaved under mild acidic condition（4 mol/L HCl in dioxane） to provide the correspondingα-difiuoromethylα-propargylamine in excellent yields（90-95%）.

关 键 词：Diasteroselectivity Difluoromethyl PROPARGYLAMINE 1 2-Addition Sulfinamides 

分 类 号：TQ433.437[化学工程] TQ655