Issue 18, 2010
From the journal:

Organic & Biomolecular Chemistry

Bifunctional thiourea-promoted cascade aza-Michael-Henry-dehydration reactions: asymmetric preparation of 3-nitro-1,2-dihydroquinolines†

Xiaoqian Liua  and  Yixin Lu*a  

* Corresponding authors

a Department of Chemistry and Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, Singapore, Republic of Singapore.
E-mail: chmlyx@nus.edu.sg
Fax: +65-6779-1691
Tel: +65-6516-1569

Abstract

A cascade aza-Michael-Henry-dehydration reaction catalyzed by quinidine-derived tertiary amine-thiourea catalyst was developed via installation of suitable electron withdrawing groups at the amino function of aniline. This strategy led to a one-step preparation of chiral 3-nitro-1,2-dihydroquinolines in high yields and with up to 90% enantiomeric excesses.

Graphical abstract: Bifunctional thiourea-promoted cascade aza-Michael-Henry-dehydration reactions: asymmetric preparation of 3-nitro-1,2-dihydroquinolines

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Article information

DOI
https://doi.org/10.1039/C0OB00223B
Article type
Communication
Submitted
07 Jun 2010
Accepted
25 Jun 2010
First published
21 Jul 2010

Org. Biomol. Chem., 2010,8, 4063-4065

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Bifunctional thiourea-promoted cascade aza-Michael-Henry-dehydration reactions: asymmetric preparation of 3-nitro-1,2-dihydroquinolines

X. Liu and Y. Lu, Org. Biomol. Chem., 2010, 8, 4063 DOI: 10.1039/C0OB00223B

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