N-Protecting group tuning of the enantioselectivity in Strecker reactions of trifluoromethyl ketimines to synthesize quaternary α-trifluoromethyl amino nitriles by ion pair catalysis

Mengyuan Du; Longhui Yu; Ting Du; Zhaokun Li; Yueyang Luo; Xiangyu Meng; Zhengtao Tian; Changwu Zheng; Weiguo Cao; Gang Zhao

doi:10.1039/C9CC09151C

N-Protecting group tuning of the enantioselectivity in Strecker reactions of trifluoromethyl ketimines to synthesize quaternary α-trifluoromethyl amino nitriles by ion pair catalysis†

Mengyuan Du,^a Longhui Yu,^b Ting Du,^b Zhaokun Li,^b Yueyang Luo,^b Xiangyu Meng,^b Zhengtao Tian,^b Changwu Zheng,*^c Weiguo Cao*^a and Gang Zhao

*^b

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* Corresponding authors

^a Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. China
E-mail: wgcao@staff.shu.edu.cn

^b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China
E-mail: zhaog@sioc.ac.cn

^c School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
E-mail: zhengcw@shutcm.edu.cn

Abstract

An enantioselective Strecker reaction to construct trifluoromethylated quaternary stereocenters with N-PMP and unexplored N-Boc trifluoromethyl ketimines catalyzed using an organophosphine dual-reagent catalyst has been developed. The enantioselectivities of the corresponding products with the same catalyst could be switched by using different N-protecting groups (N-PMP or N-Boc). The trifluoromethyl amino nitriles were obtained in high yield and high enantioselectivity in a short time and could be easily converted to a variety of useful trifluoromethyl-containing compounds.

Chemical Communications

N-Protecting group tuning of the enantioselectivity in Strecker reactions of trifluoromethyl ketimines to synthesize quaternary α-trifluoromethyl amino nitriles by ion pair catalysis†

Abstract

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N-Protecting group tuning of the enantioselectivity in Strecker reactions of trifluoromethyl ketimines to synthesize quaternary α-trifluoromethyl amino nitriles by ion pair catalysis

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