Copper-Catalyzed Asymmetric Aminocyanation of Arylcyclopropanes for Synthesis of γ-Amino Nitriles

被引：77
|
作者：
Yang, Shengbiao [1 ]
Wang, Lihong [1 ]
Zhang, Hongwei [2 ]
Liu, Chunyang [1 ]
Zhang, Linli [1 ]
Wang, Xiaomin [1 ]
Zhang, Ge [1 ]
Li, Yan [1 ]
Zhang, Qian [1 ]
机构：
[1] Northest Normal Univ, Dept Chem, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Jilin, Peoples R China
[2] China Univ Petr East China, Coll Sci, Qingdao 266580, Peoples R China
来源：
ACS CATALYSIS | 2019年 / 9卷 / 01期
基金：
中国国家自然科学基金;
关键词：
copper catalyst; asymmetric aminocyanation; cyclopropanes; gamma-amino nitriles; radical cation; 3-ELECTRON S(N)2 REACTIONS; LEWIS-ACID CATALYSIS; CYCLOPROPYL KETONES; ENANTIOSELECTIVE SYNTHESIS; PHOTOCHEMICAL ADDITION; ALKYLATION REACTIONS; CATION RADICALS; CYANATION; GABA; ALKENES;
D O I：
10.1021/acscatal.8b03768
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A facile approach for the synthesis of enantiopure gamma-amino nitriles by copper-catalyzed amino-cyanation of arylcyclopropanes is disclosed, which undergoes the highly enantioselective ring-opening reaction of cyclopropanes. The strategy utilizes N-fluorobenzenesulfonimide as nucleophilic nitrogen source as well as oxidant and trimethylsilyl cyanide as the other nucleophile, and it probably operates via a key radical cation intermediate. This reaction provides an efficient platform for asymmetric 1,3-difunctionalization of cyclopropanes.
引用
收藏
页码：716 / 721
页数：11
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