Asymmetric Intramolecular Oxa-Michael Reactions of Cyclohexadienones Catalyzed by a Primary Amine Salt

被引：102

作者：

Wu, Wenbin ^{[1
]}

Li, Xin ^{[1
]}

Huang, Huicai ^{[1
]}

Yuan, Xiaoqian ^{[1
]}

Lu, Junzhu ^{[1
]}

Zhu, Kailong ^{[1
]}

Ye, Jinxing ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Minist Educ, Sch Pharm, Shanghai 200237, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 06期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; cyclohexadienones; iminium activation; Michael addition; primary amine salt; FRIEDEL-CRAFTS ALKYLATION; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; ALPHA; BETA-UNSATURATED KETONES; CONJUGATE ADDITION; STEREOSELECTIVE-SYNTHESIS; ORGANIC CATALYSIS; CONCISE SYNTHESIS; CASCADE REACTIONS; DESYMMETRIZATION;

D O I：

10.1002/anie.201206977

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Michael brings the rings: An asymmetric intramolecular oxa-Michael reaction involving iminium activation has been developed. This reaction provides enantioenriched 1,4-dioxane derivatives with up to 99 % yield and 98 % ee. The method allows for concise and stereoselective access to stereodiverse, complex tetracyclic compounds containing a bicyclo[2.2.2]octan-2-one backbone with multiple chiral centers. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1743 / 1747

页数：5

共 123 条

[1] Highly diastereoselective oxy-Michael additions of enantiopure δ-lactol anions to nitroalkenes:: Asymmetric synthesis of 1,2-amino alcohols [J].