Selective Condensation of titanium Reagent with Carbonyl Compounds

Article abstract of DOI:10.1246/bcsj.57.2781

<3-(Ethylthio)allyl>titanium reagent generated easily from allyl ethyl sulfides condensed with aldehydes to give erythro-β-hydroxy sulfides in highly regio- and stereoselective manner.In contrast, crotyl ethyl sulfide reacted with aldehydes affording δ-hydroxy vinyl sulfide exclusively.The substitution pattern of the starting sulfide can have a pronounced effect on the selectivity in this condensation reaction, erythro-β-Hydroxy sulfide obtained was transfromed stereoselectively to the trans-vinyloxirane or 1,3-alkadiene.