文献类型：期刊文献

英文题名：Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts

作者：Wang, Yan[1,2];Liu, Yunlong[1,2];Zhang, Dongdong[1,2];Wei, Hao[3];Shi, Min[1,2,4];Wang, Feijun[1,2]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Shanghai Jiao Tong Univ, Sch Elect Informat & Elect Engn, Shanghai 200240, Peoples R China;[4]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China

年份：2016

卷号：55

期号：11

起止页码：3776

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20160902026722);WOS:【SCI-EXPANDED(收录号:WOS:000371521000044)，CCR-EXPANDED(收录号:WOS:000371521000044)】；

基金：We acknowledge the National Natural Science Foundation of China (21372075 and 61376003) and the Medical-Engineering Crossover Fund of Shanghai Jiao Tong University (YG2015MS23) for financial support, and also give thanks to Dr. Abraha Habtemariam at Department of Chemistry, University of Warwick for revision of this manuscript.

语种：英文

外文关键词：boron; heterocycles; nucleophilic addition; rhodium; total synthesis

摘要：A highly enantioselective rhodium(I)-catalyzed dearomative arylation or alkenylation of easily available N-alkylquinolinium salts is reported, thus providing an effective and practical approach to the synthesis of dihydroquinolines in up to 99%ee. This reaction tolerates a wide range of functional groups with respect to both the organic boronic acids and the quinoline starting materials. Moreover, the synthetic utility of this protocol is demonstrated in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (-)-angustureine and (+)-cuspareine.