Regio- and stereoselective homolytic hydrostannylation of propargyl alcohols and ethers with dibutylchlorostannane.

J Org Chem

Department of Chemistry, 21st Century COE, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.

Published: October 2003


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Article Abstract

The Et3B-initiated reaction of gamma-unsubstituted propargyl alcohols with dibutylchlorostannane (Bu2SnClH) at low temperature gave (Z)-vinylstannanes with high regio- and stereoselectivity. The corresponding alkyl propargyl ethers also underwent regio- and stereoselective homolytic hydrostannylation with Bu2SnClH; however, the regioselectivity was not so high as that with the propargyl alcohols.

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http://dx.doi.org/10.1021/jo035012sDOI Listing

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