Issue 19, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Diastereoselective radical allylation and hydrogenation of α-(arylsulfinyl)alkyl radicals induced by chelation control

Nobuyuki Mase,†a   Yoshihiko Watanabe,‡a   Koji Higuchi,a   Shuichi Nakamuraa  and  Takeshi Toru*a  

* Corresponding authors

a Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Nagoya 466-8555, Japan
E-mail: toru@ach.nitech.ac.jp
Fax: 81-52-735-5217
Tel: 81-52-735-5217

Abstract

The radical allylation and the hydrogenation of α-(arylsulfinyl)alkyl radicals were examined. In the presence of a bidentate Lewis acid, high diastereoselectivities were achievable in the allylation and the hydrogenation of α-(arylsulfinyl)alkyl radicals derived through the radical β-addition to vinyl sulfoxides bearing the 2-pyridyl, the imidazol-2-yl, or the benzimidazol-2-yl groups.

Graphical abstract: Diastereoselective radical allylation and hydrogenation of α-(arylsulfinyl)alkyl radicals induced by chelation control

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Article information

DOI
https://doi.org/10.1039/B207249A
Article type
Communication
Submitted
24 Jul 2002
Accepted
23 Aug 2002
First published
05 Sep 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2134-2136

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Diastereoselective radical allylation and hydrogenation of α-(arylsulfinyl)alkyl radicals induced by chelation control

N. Mase, Y. Watanabe, K. Higuchi, S. Nakamura and T. Toru, J. Chem. Soc., Perkin Trans. 1, 2002, 2134 DOI: 10.1039/B207249A

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