Issue 5, 2006
From the journal:

Chemical Communications

Unprecedented 1,4-stannatropy: effective generation of azomethine ylides as nitrile ylide equivalents from N-(stannylmethyl)thioamides†

Mitsuo Komatsu,‡*a   Yukihiro Kasano,b   Jin-ichi Yonemori,b   Yoji Oderaotoshib  and  Satoshi Minakatab  

* Corresponding authors

a Department of Applied Chemistry and Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, Japan
E-mail: komatsu@chem.eng.osaka-u.ac.jp
Fax: +81-6-6879-7402

b Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, Japan

Abstract

Generation and cycloaddition of less- or non-stabilized azomethine ylides, or nitrile ylide equivalents, via unprecedented 1,4-stannatropy of N-(tributylstannylmethyl)thioamides were achieved. The reactions with dipolarophiles, such as electron-deficient alkenes and alkynes, afforded corresponding pyrrolidine and pyrrole derivatives effectively.

Graphical abstract: Unprecedented 1,4-stannatropy: effective generation of azomethine ylides as nitrile ylide equivalents from N-(stannylmethyl)thioamides

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Article information

DOI
https://doi.org/10.1039/B513413G
Article type
Communication
Submitted
22 Sep 2005
Accepted
17 Nov 2005
First published
13 Dec 2005

Chem. Commun., 2006, 526-528

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Unprecedented 1,4-stannatropy: effective generation of azomethine ylides as nitrile ylide equivalents from N-(stannylmethyl)thioamides

M. Komatsu, Y. Kasano, J. Yonemori, Y. Oderaotoshi and S. Minakata, Chem. Commun., 2006, 526 DOI: 10.1039/B513413G

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