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
收藏
页码：913 / 917
页数：5
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