Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts

Yan Wang; Yunlong Liu; Dongdong Zhang; Hao Wei; Min Shi; Feijun Wang

doi:10.1002/anie.201511663

Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts

Angew Chem Int Ed Engl. 2016 Mar 7;55(11):3776-80. doi: 10.1002/anie.201511663. Epub 2016 Feb 16.

Authors

Yan Wang¹, Yunlong Liu¹, Dongdong Zhang¹, Hao Wei², Min Shi^{1

3}, Feijun Wang⁴

Affiliations

¹ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P.R. China.
² School of Electronic Information and Electrical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, P.R. China. haowei@sjtu.edu.cn.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, P.R. China.
⁴ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P.R. China. feijunwang@ecust.edu.cn.

PMID: 26879692
DOI: 10.1002/anie.201511663

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.

Keywords: boron; heterocycles; nucleophilic addition; rhodium; total synthesis.

Publication types

Research Support, Non-U.S. Gov't