Issue 16, 2013
From the journal:

Organic & Biomolecular Chemistry

The Staudinger reaction with 2-imino-1,3-thiaselenanes toward the synthesis of C4 spiro-β-lactams†

Yosuke Toyoda,‡a   Masayuki Ninomiya,b   Masahiro Ebiharaa  and  Mamoru Koketsu*b  

* Corresponding authors

a Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu, Japan

b Department of Materials Science and Technology, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu, Japan
E-mail: koketsu@gifu-u.ac.jp
Fax: (+81) 58-293-2794

Abstract

The Staudinger ketene–imine [2 + 2] cycloaddition reaction for conversion of α-heteroatom-substituted exocyclic imines to C4 heterocyclic spiro-β-lactams has rarely been investigated due to their instability. Herein, we describe the Staudinger reaction between ketenes and α-selenium-substituted exocyclic imines to synthesize C4 spiro-β-lactams.

Graphical abstract: The Staudinger reaction with 2-imino-1,3-thiaselenanes toward the synthesis of C4 spiro-β-lactams

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Article information

DOI
https://doi.org/10.1039/C3OB00073G
Article type
Paper
Submitted
14 Jan 2013
Accepted
05 Feb 2013
First published
05 Feb 2013

Org. Biomol. Chem., 2013,11, 2652-2659

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The Staudinger reaction with 2-imino-1,3-thiaselenanes toward the synthesis of C4 spiro-β-lactams

Y. Toyoda, M. Ninomiya, M. Ebihara and M. Koketsu, Org. Biomol. Chem., 2013, 11, 2652 DOI: 10.1039/C3OB00073G

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