Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts

Angewandte Chemie
Yan WangFeijun Wang

Abstract

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.

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Citations

Dec 17, 2016·Chemical Communications : Chem Comm·Mao QuanWanbin Zhang
Dec 22, 2017·Organic & Biomolecular Chemistry·Jianqiao Zhou, Hexin Xie
Nov 28, 2017·Chemistry : a European Journal·Sunisa AkkarasamiyoJoseph S M Samec
Jun 10, 2018·Nature Communications·Mao QuanWanbin Zhang
Apr 10, 2019·Chemical Reviews·Isravel MuthukrishnanJ Carlos Menéndez
Aug 16, 2017·The Journal of Organic Chemistry·Stephen G DaviesJames E Thomson
Mar 28, 2019·Journal of the American Chemical Society·Ran LuLei Liu
Nov 11, 2020·Journal of the American Chemical Society·Xingchen YanSyuzanna R Harutyunyan
Nov 24, 2021·Journal of the American Chemical Society·Shao-Jie LouZhaomin Hou
Jan 11, 2022·Journal of the American Chemical Society·Peng YangYi-Xia Jia

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