Bifunctional cinchona alkaloid-squaramide-catalyzed highly enantioselective aza-Michael addition of indolines to α,β-unsaturated ketones

被引：16
|
作者：
Ghosh, Arun K. [1 ]
Zhou, Bing [1 ]
机构：
[1] Purdue Univ, Dept Chem & Med Chem, W Lafayette, IN 47907 USA
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 27期
基金：
美国国家卫生研究院;
关键词：
Aza-Michael reaction; Organocatalysis; Indoline; beta-Keto indoline; Cinchona alkaloid; Enantioselective; FRIEDEL-CRAFTS ALKYLATION; CHIRAL PHOSPHORIC-ACIDS; BETA-AMINO ACIDS; CONJUGATE ADDITION; N-HETEROCYCLES; 1,3-DICARBONYL COMPOUNDS; ALLYLIC ALKYLATION; MANNICH REACTION; BRONSTED ACIDS; INDOLES;
D O I：
10.1016/j.tetlet.2013.04.080
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective aza-Michael addition of indolines to alpha,beta-unsaturated ketones was achieved using a bifunctional cinchona alkaloid-derived chiral squaramide derivative. Various beta-indolinyl ketone derivatives were obtained in good to excellent yields and with high enantioselectivity. DDQ or MnO2 oxidation of indoline derivatives provided convenient access to various enantioenriched N-substituted indole derivatives. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3500 / 3502
页数：3
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