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Synthesis 2017; 49(14): 3157-3164
DOI: 10.1055/s-0036-1589012
paper
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Reduction of 3-Substituted Quinolines with a Cyclopentadiene-Based Chiral Brønsted Acid

Xiaofang Zhao
a   Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, and School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi’an, 710119, P. R. of China   Email: tangwj@snnu.edu.cn
,
Jianliang Xiao
a   Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, and School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi’an, 710119, P. R. of China   Email: tangwj@snnu.edu.cn
b   Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK
,
Weijun Tang  *
a   Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, and School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi’an, 710119, P. R. of China   Email: tangwj@snnu.edu.cn
› Author AffiliationsWe are grateful for the financial support of the National Science Foundation of China (21302116), the Fundamental Research Funds for the Central Universities (GK201703018), and Shaanxi Normal University.
Further Information

Publication History

Received: 04 February 2017

Accepted after revision: 29 March 2017

Publication Date:
08 May 2017 (online)

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Abstract

Enantioselective reduction of 3-substituted quinolines has been achieved using a cyclopentadiene-based chiral Brønsted acid as catalyst and Hantzsch ester as hydrogen donor, affording the corresponding tetrahydroquinolines in good enantioselectivities.

Key words

tetrahydroquinolines - transfer hydrogenation - 3-substituted quinolones - enantioselectivity - chiral Brønsted acid

Supporting Information

    Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589012.
  • Supporting Information
 

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