Tandem Michael addition–carbene insertion reaction of 1-alkynyl(aryl)(tetrafluoroborato)-λ3-bromanes: 1-(phenylsulfonyl)- and 1-(trifluoromethylsulfonyl)cyclopentene annulation

Masahito Ochiai; Norihiro Tada; Yoshio Nishi; Kentaro Murai

doi:10.1039/B410830B

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Tandem Michael addition–carbeneinsertion reaction of 1-alkynyl(aryl)(tetrafluoroborato)-λ³-bromanes: 1-(phenylsulfonyl)- and 1-(trifluoromethylsulfonyl)cyclopentene annulation

Masahito Ochiai,*^a Norihiro Tada,^a Yoshio Nishi^a and Kentaro Murai^a

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* Corresponding authors

^a Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima, Japan
E-mail: mochiai@ph.tokushima-u.ac.jp
Fax: +81 88 633 9504
Tel: +81 88 633 7281

Abstract

Exposure of 1-alkynyl[p-(trifluoromethyl)phenyl](tetrafluoroborato)-λ³-bromanes to sodium benzenesulfinate or sodium trifluoromethanesulfinate in dichloromethane at 0 °C under argon resulted in tandem Michael–carbene insertion reactions to produce 1-sulfonylcyclopentenes selectively, with concomitant formation of a small amount of rearranged 1-alkynyl sulfones.

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Article information

DOI: https://doi.org/10.1039/B410830B
Article type: Communication
Submitted: 19 Jul 2004
Accepted: 17 Aug 2004
First published: 27 Sep 2004

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Chem. Commun., 2004, 2894-2895

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Tandem Michael addition–carbene insertion reaction of 1-alkynyl(aryl)(tetrafluoroborato)-λ³-bromanes: 1-(phenylsulfonyl)- and 1-(trifluoromethylsulfonyl)cyclopentene annulation

M. Ochiai, N. Tada, Y. Nishi and K. Murai, Chem. Commun., 2004, 2894 DOI: 10.1039/B410830B

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