文献类型：期刊文献

英文题名：An Organocatalytic Cascade Approach toward Polysubstituted Quinolines and Chiral 1,4-Dihydroquinolines-Unanticipated Effect of N-Protecting Groups

作者：Zhang, Xinshuai[3];Song, Xixi[3];Li, Hao[1,2];Zhang, Shilei[3];Chen, Xiaobei[3];Yu, Xinhong[1,2];Wang, Wei[1,2,3]

机构：[1]E China Univ Sci & Technol, Shanghai Key Lab New Drug Design, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[3]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2012

卷号：51

期号：29

起止页码：7282

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20122915263511);WOS:【SCI-EXPANDED(收录号:WOS:000306314300044)，CCR-EXPANDED(收录号:WOS:000306314300044)】；

基金：Financial support of this research is provided by the National Science Foundation (CHE-1057569, W. W.) and ECUST (W. W.), the China 111 Project (Grant B07023, W. W.), NSFC (20972051, X.-H.Y.), the Science and Technology Commission of Shanghai Municipality (08430703900 and 08431901800, X.-H.Y.), and the Shanghai Committee of Science and Technology (Grant 11DZ2260600).

语种：英文

外文关键词：1; 4-dihydroquinolines; cascade reactions; divergent synthesis; organocatalysis; quinolines

摘要：A matter of protection: The outcome of a divergent organocatalytic aza-Michael/aldol cascade process toward quinolines and 1,4-dihydroquinolines depends on the choice of the N-protecting group (see scheme; TEA=triethylamine, TMS=trimethylsilyl). Use of an electron-donating sulfonyl group results in an unanticipated aza-Michael/aldol/aromatization cascade to give polysubstituted quinolines (right). In contrast, chiral 1,4-dihydroquinolines are obtained with an electron-withdrawing sulfonyl group (left). Copyright ? 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.