Synthesis and Diels-Alder reactions of t-butyl and t-butyl, methyl (S)s-2-p-tolylsulfinylmaleates, chiral synthetic equivalents of monoalkyl and mixed dialkyl acetylenedicarboxylates

Article abstract of DOI:10.1016/S0040-4039(00)92127-0

The reaction of t-butyl p-tolylsulfinylacetate with glyoxylic acid yielded maleate monoester 1, whose methylation afforded asymmetric diester 2. Conditions in which 1 and 2 react with cyclopentadiene exhibiting high facial and endo selectivities are reported.