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

页码：703 / 708

页数：6

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