Synthesis of Chiral α-Trifluoromethylamines with 2,2,2-Trifluoroethylamine as a “Building Block”

• DOI: 10.1021/acs.orglett.5b03566
• Publication Date: 2016-02-16T15:03:58Z
• Authors: Xiaoyuan Li; Jinhuan Su; Zhourujun Liu; Yuanyuan Zhu; Zhenghao Dong; Shuai Qiu; Jiayi Wang; Li Lin; Zhiqiang Shen; Wenjin Yan; Kairong Wang; Rui Wang
• Keywords: SN2 reaction; Cinchonine

The β-isocupreidine, a cinchonine derived alkaloid, catalyzed asymmetric SN2′–SN2′ reaction between N-2,2,2-trifluoroethylisatin ketimines and MBH type carbonates was realized in simple efficient way. A series of chiral α-trifluoromethylamines were prepared with excellent yields stereoselectivities. subsequent easy process deprotection gave γ-trifluoromethyl-α-methylenelactam stereoselective manner.