An Organocatalytic, δ-Regioselective, and Highly Enantioselective Nucleophilic Substitution of Cyclic Morita-Baylis-Hillman Alcohols with Indoles

被引：50
|
作者：
Qiao, Zhen [1 ]
Shafiq, Zahid [1 ]
Liu, Li [1 ]
Yu, Zheng-Bao [1 ]
Zheng, Qi-Yu [1 ]
Wang, Dong [1 ]
Chen, Yong-Jun [1 ]
机构：
[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, BNLMS, Beijing 100190, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 40期
基金：
中国国家自然科学基金;
关键词：
indoles; Morita-Baylis-Hillman alcohols; nucleophilic substitution; organocatalysis; delta regioselectivity; FRIEDEL-CRAFTS ALKYLATION; SIMPLE ALPHA; BETA-UNSATURATED KETONES; CONJUGATE ADDITION-ELIMINATION; ACTIVATED ALLYLIC ACETATES; MICHAEL ADDITION; ASYMMETRIC AMINOCATALYSIS; KINETIC RESOLUTION; GAMMA-BUTENOLIDES; CASCADE REACTION; FURAQUINOCIN-E;
D O I：
10.1002/anie.201003131
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The unexpected becomes possible: The first enantioselective, direct nucleophilic substitution of Morita-Baylis-Hillman alcohols has been developed through the use of iminium catalysis. Unexpected δ-substituted products were obtained with exclusive regioselectivity and high enantioselectivity for the reaction of cyclopent-2-enone-derived alcohols with indoles catalyzed by 1. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：7294 / 7298
页数：5
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