Issue 7, 2015
From the journal:

New Journal of Chemistry

Enantioselective synthesis of functionalized 3,4-disubstituted dihydro-2(1H)-quinolinones via Michael–hemiaminalization/oxidation reaction†

Ai-Bao Xia,a   Xiao-Long Zhang,a   Tao Wang,a   Xiao-Hua Du,a   Dan-Qian Xu*a  and  Zhen-Yuan Xu*a  

* Corresponding authors

a Catalytic Hydrogenation Research Centre, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, China
E-mail: chrc@zjut.edu.cn, greenchem@zjut.edu.cn

Abstract

A novel method is developed for the enantioselective synthesis of highly functionalized 3,4-disubstituted dihydro-2(1H)-quinolinones bearing two trans contiguous stereogenic centers with excellent diastereoselectivities (up to >99 : 1 dr) and high to excellent enantioselectivities (up to >99% ee). The process combines an enantioselective organocatalytic Michael–hemiaminalization reaction and a highly efficient oxidation reaction sequence with good yields and stereoselectivity.

Graphical abstract: Enantioselective synthesis of functionalized 3,4-disubstituted dihydro-2(1H)-quinolinones via Michael–hemiaminalization/oxidation reaction

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Article information

DOI
https://doi.org/10.1039/C4NJ01718H
Article type
Letter
Submitted
03 Oct 2014
Accepted
04 May 2015
First published
05 May 2015

New J. Chem., 2015,39, 5088-5091

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Enantioselective synthesis of functionalized 3,4-disubstituted dihydro-2(1H)-quinolinones via Michael–hemiaminalization/oxidation reaction

A. Xia, X. Zhang, T. Wang, X. Du, D. Xu and Z. Xu, New J. Chem., 2015, 39, 5088 DOI: 10.1039/C4NJ01718H

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