A highly enantioselective approach to functionalized [4.n.0] bicyclic compounds

Abstract The Diels-Alder reaction of benzyl, methyl (S)-2-( p -tolylsulfinyl) maleate with several 1-vinylcycloalkenes, catalyzed by TiCl 4 , occurred with complete regio and stereoselectivity. The regioselectivity of the sulfinyl elimination from the adducts, as well as the stereoselectivity of the epoxidation and the hydroboration of the resulting [4.n.0] bicyclic compounds, increase with the size of the second ring.