Asymmetric Allylic Amination of Morita-Baylis-Hillman Adducts with Simple Aromatic Amines by Nucleophilic Amine Catalysis

被引：10
|
作者：
Zhao, Shuai [1 ]
Chen, Zhi-Li [1 ]
Rui, Xue [1 ]
Gao, Ming-Mei [1 ]
Chen, Xin [1 ]
机构：
[1] Changzhou Univ, Sch Pharmaceut Engn & Life Sci, Changzhou 213164, Peoples R China
来源：
SYNLETT | 2019年 / 30卷 / 06期
基金：
美国国家科学基金会;
关键词：
MBH adducts; aromatic amines; asymmetric allylic amination; nucleophilic amine catalysis; inorganic fluorides; KINETIC RESOLUTION; FACILE ACCESS; CARBONATES; ACETATES; ACID; CONSTRUCTION; SUBSTITUTION; ANNULATIONS; DERIVATIVES; ALKYLATION;
D O I：
10.1055/s-0037-1611740
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric allylic amination of Morita-Baylis-Hillman (MBH) adducts with simple aromatic amines is successfully realized by nucleophilic amine catalysis. A range of substituted -methylene--arylamino esters is accessed in moderate to high yields (up to 88%) and with excellent enantioselectivities (up to 97% ee). Inorganic fluorides are found to be able to improve the enantioselectivity of the allylic amination reaction. A pyrrole-2-carboxylate and a cyclic imide are also compatible with this catalytic system. A chiral 2,3-dihydroquinolin-4-one derivative is easily obtained from the allylic amination product.
引用
收藏
页码：703 / 708
页数：6
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