Enantioselective Michael Addition of 4-Hydroxycoumarins to β,γ-Unsaturated α-Oxophosphonates Catalysed by a Bifunctional Squaramide Bearing a Structurally Rigid 9,10-Ethylene-9,10-dihydroanthracene Skeleton

被引：15

作者：

Chang, Xufang ^{[1
]}

Wang, Qiaohui ^{[1
]}

Wang, Youming ^{[1
]}

Song, Haibin ^{[1
]}

Zhou, Zhenghong ^{[1
]}

Tang, Chuchi ^{[1
]}

机构：

[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 11期

基金：

中国国家自然科学基金;

关键词：

Enantioselectivity; Oxygen heterocycles; Michael addition; Asymmetric catalysis; Organocatalysis; ANTI-AIDS AGENTS; CYCLIC 1,3-DICARBONYL COMPOUNDS; ALPHA; BETA-UNSATURATED IMIDES; CONJUGATE ADDITION; HIV ACTIVITY; 4-HYDROXYPYRONE; ORGANOCATALYSIS; NITROALKANES; KETONES;

D O I：

10.1002/ejoc.201201573

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bifunctional squaramide based on (R,R)-11,12-diamino-9,10-ethylene-9,10-dihydroanthracene has been developed, and it has demonstrated great advantages over previously reported organocatalysts in the asymmetric Michael addition of 4-hydroxycoumarins to beta,gamma-unsaturated alpha-oxophosphonates. Upon quenching the generated beta-4-hydroxy-2-oxo-2H-chromen-3-yl-substituted acylphosphonate intermediates with DBU and an alcohol or amine as a second nucleophile, the corresponding beta-substituted carboxylates or amides were obtained in acceptable to excellent yields and with high levels of enantioselectivity (80-97% ee) in a one-pot fashion.

引用

页码：2164 / 2171

页数：8

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