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

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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.
Chemical Communications ( IF 4.3 ) Pub Date : 2020-01-14 , DOI: 10.1039/c9cc09151c
Mengyuan Du ₁ , Longhui Yu ₂ , Ting Du ₂ , Zhaokun Li ₂ , Yueyang Luo ₂ , Xiangyu Meng ₂ , Zhengtao Tian ₂ , Changwu Zheng ₃ , Weiguo Cao ₁ , Gang Zhao ₂

Affiliation

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.

中文翻译：

N保护基对三氟甲基酮亚胺在Strecker反应中通过离子对催化合成α-三氟甲基氨基腈的对映选择性的调节。

已开发出一种对映选择性斯特雷克反应，该反应可利用有机膦双试剂催化剂与N-PMP和未探索的N-Boc三氟甲基酮亚胺构建三氟甲基化的季立体中心。可以通过使用不同的N保护基（N-PMP或N-Boc）来切换相应产物与相同催化剂的对映选择性。在短时间内以高收率和高对映选择性获得了三氟甲基氨基腈，并且可以容易地将其转化为多种有用的含三氟甲基的化合物。

更新日期：2020-01-14

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