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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