Synthesis and Diels Alder Reactions of (+)-(S)-1-t-Butylsulfonyl-1-p-Tolylsulfinylethene, a New Masked Chiral Ketene Equivalent

Article abstract of DOI:10.1016/S0957-4166(00)80525-X

Enantiomerically pure (+)-(S)s-1-t-butylsulfonyl-1-p-tolylsulfinylethene (1) was easily prepared in three steps from t-butyl methyl sulfone.The catalyzed Diels-Alder reactions of 1 with cyclopentadiene were highly stereoselective.The major adduct was transformed into (+)-(1R,4R)-dehydronorcamphor and (+)-(1R,4S)-2-t-butylsulfonyl-2,5-norbornadiene.