Issue 5, 2008
From the journal:

Organic & Biomolecular Chemistry

Crystallization-induced diastereomer transformation of 2-quinolone-4-carboxamide followed by stereoselective intermolecular photocycloaddition reaction†‡§

Masami Sakamoto,*a   Naoto Sato,a   Takashi Mino,a   Yoshio Kasashimaa  and  Tsutomu Fujitaa  

* Corresponding authors

a Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, Japan
E-mail: sakamotom@faculty.chiba-u.jp
Fax: +81 43 290 3401
Tel: +81 43 290 3387

Abstract

2-Quinolone-4-carboxamide derived from (S)-proline, which exists as a mixture of two diastereomers before crystallization, converged to a single diastereomer by crystallization (CIDT), and the homochirality was transferred by a intermolecular 2 + 2 photocycloaddition reaction with high optical activity.

Graphical abstract: Crystallization-induced diastereomer transformation of 2-quinolone-4-carboxamide followed by stereoselective intermolecular photocycloaddition reaction

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Article information

DOI
https://doi.org/10.1039/B719761F
Article type
Communication
Submitted
21 Dec 2007
Accepted
22 Jan 2008
First published
04 Feb 2008

Org. Biomol. Chem., 2008,6, 848-850

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Crystallization-induced diastereomer transformation of 2-quinolone-4-carboxamide followed by stereoselective intermolecular photocycloaddition reaction

M. Sakamoto, N. Sato, T. Mino, Y. Kasashima and T. Fujita, Org. Biomol. Chem., 2008, 6, 848 DOI: 10.1039/B719761F

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