Homochiral Matching in the Diels-Alder Cyclodimerization of 2-Vinyl-7-oxabicyclohept-2-ene Derivatives.

Article abstract of DOI:10.1016/0040-4039(94)88176-6

Keywords: Face selectivity, <4+2>-cycloadditions, chiral recognition, (1R,2S,3S,4R,7R,11S,12R)-11-ethenyl-15,16-dioxapentacyclo<10.2.1.1.^4,7.0^3,8.0^2,11>hexadec-8-en-6,13-dione, (1R,2R,3R,4R,7R,11R,12R)-11-ethenyl-15,16-dioxapentacyclo<10.2.1.1.^4,7.0^3,8.0^2,11>hexadec-8-en-5,14-dione and their ethylene acetals.Abstract: Racemic 6-vinyl-7-oxabicyclo<2.2.1>hept-5-en-2-one, 5-vinyl-7-oxabicyclo<2.2.1>hept-5-en-2-one and their ethylene acetals undergo highly stereoselective Diels-Alder cyclodimerizations.The optically pure semicyclic dienes give the corresponding optically pure dimers with the same ease.