Issue 53, 2020
From the journal:

Chemical Communications

Biomimetic asymmetric reduction of benzoxazinones and quinoxalinones using ureas as transfer catalysts†

Zi-Biao Zhao, ORCID logo ab   Xiang Li,a   Mu-Wang Chen, ORCID logo c   Zongbao K. Zhao ORCID logo *c  and  Yong-Gui Zhou ORCID logo *abc  

* Corresponding authors

a Zhang Dayu School of Chemistry, Dalian University of Technology, Dalian 116024, P. R. China

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China

c State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China
E-mail: zhaozb@dicp.ac.cn, ygzhou@dicp.ac.cn

Abstract

Using ureas as transfer catalysts through hydrogen bonding activation, biomimetic asymmetric reduction of benzoxazinones and quinoxalinones with chiral and regenerable NAD(P)H models was described, giving chiral dihydrobenzoxazinones and dihydroquinoxalinones with high yields and excellent enantioselectivities. A key dihydroquinoxalinone intermediate of a BRD4 inhibitor was synthesized using biomimetic asymmetric reduction.

Graphical abstract: Biomimetic asymmetric reduction of benzoxazinones and quinoxalinones using ureas as transfer catalysts

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Article information

DOI
https://doi.org/10.1039/D0CC03091K
Article type
Communication
Submitted
29 Apr 2020
Accepted
21 May 2020
First published
27 May 2020

Chem. Commun., 2020,56, 7309-7312

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Biomimetic asymmetric reduction of benzoxazinones and quinoxalinones using ureas as transfer catalysts

Z. Zhao, X. Li, M. Chen, Z. K. Zhao and Y. Zhou, Chem. Commun., 2020, 56, 7309 DOI: 10.1039/D0CC03091K

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