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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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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.

Graphical abstract: 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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Article information


Submitted
25 Nov 2019
Accepted
02 Jan 2020
First published
03 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

M. Du, L. Yu, T. Du, Z. Li, Y. Luo, X. Meng, Z. Tian, C. Zheng, W. Cao and G. Zhao, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09151C

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