The ability of a homochiral sulfinyl group at the dienophile to act as a remote stereocontrol inductor in the Diels-Alder reaction with cyclopentadiene has been evaluated. High pressure conditions were required for the reactions of (S)-2-(p-tolylsulfinyl)styrenes 3-5 (E-1,2-disubstituted double bond) and 6-8 (1,1-disubstituted double bond). A good facial selectivity and total endo selectivity were attained with 1,1-disubstitued dienophiles, though the 1,2-disubstituted ones afforded poorer results. In contrast, (S)-[2-(p-tolylsulfinyl)phenyl] vinyl ketones 9-11 reacted readily at low temperature (-40 degrees C) with complete endo selectivity and high facial selectivity in the presence of Yb(OTf)(3) as a chelating reagent of sulfinyl and carbonyl oxygen atoms. Concerning furan reactions, beta-trifluoromethyl enone 14 afforded Diels Alder adducts with high facial selectivity in the presence of the Lewis acid, but beta-non-substituted enones 9 and 12 yielded products of furan conjugate addition to the double bond. (C) 2012 Elsevier Ltd. All rights reserved.