Organocatalyzed asymmetric synthesis and absolute configuration assignment of enantioenriched α-benzylaminocoumarins

被引：12

作者：

Lin, Hua ^{[1
]}

Tan, Yu ^{[1
]}

Wu, Jian-Ming ^{[1
]}

Yang, Xiao-Di ^{[2
]}

Chen, Jun-Hua ^{[1
]}

Sun, Xing-Wen ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Fudan Univ, Adv Mat Lab, Shanghai 200433, Peoples R China

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 07期

基金：

中国国家自然科学基金;

关键词：

Organocatalysis; Cinchona alkaloid; Mannich reaction; Chiral amine; Coumarin; MANNICH-TYPE REACTION; ENANTIOSELECTIVE SYNTHESIS; COUMARIN DERIVATIVES; CINCHONA ALKALOIDS; ORGANIC CATALYSIS; KETO-ESTERS; EFFICIENT; IMINES; LEVOCETIRIZINE; STEREOCENTERS;

D O I：

10.1016/j.tetlet.2014.12.138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cinchona alkaloid catalyzed asymmetric Mannich reaction of 4-hydroxycoumarins and N-p-tolylsulfinylimines was achieved to synthesize enantioenriched alpha-benzylaminocoumarins in moderate to excellent yields (up to 99%) and with moderate to good enantioselectivities (up to 83% ee). The absolute configuration of the resulting chiral amines was assigned by analysis of computational and experimental electronic circular dichroism (ECD) spectroscopies. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：913 / 917

页数：5

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