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

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...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2020-02, Vol.56 (10), p.1581-1584
Hauptverfasser: Du, Mengyuan, Yu, Longhui, Du, Ting, Li, Zhaokun, Luo, Yueyang, Meng, Xiangyu, Tian, Zhengtao, Zheng, Changwu, Cao, Weiguo, Zhao, Gang
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Sprache:eng
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc09151c