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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
› InstitutsangabenWe 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.
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Publikationsverlauf

Received: 04. Februar 2017

Accepted after revision: 29. März 2017

Publikationsdatum:
08. Mai 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