(S,S)-1,1-bis-ethoxycarbonyl-2,2-bis-p-tolylsulfinyl ethene: A highly stereoselective but unexpectedly unreactive dienophile in asymmetric Diels-Alder reactions

Article abstract of DOI:10.1016/S0957-4166(96)00526-5

The synthesis and dienophilic behaviour of (S,S)-1,1-bis-ethoxycarbonyl-2,2-bis-p-tolylsulfinyl ethene with cyclic and acyclic dienes is reported. The stereoselectivity is high with cyclopentadiene and complete with acyclic dienes, but its reactivity is unexpectedly low, requiring high pressures (13 Kbar) to evolve into the corresponding adducts or their pyrolytic sulfinyl elimination products.