Phosphine-catalyzed Rauhut-Currier reaction of γ-alkyl allenoate and subsequent trapping using the Diels-Alder reaction.

We have disclosed a Rauhut-Currier reaction of γ-alkyl-substituted allenoate, catalyzed by L-valine-derived amide phosphine, to form trisubstitued allenoate, which was trapped by maleimide or DMAD via the Diels-Alder reaction. Exo -bicyclic succinimide derivatives including three continuous stereocenters with an exo -carbon-carbon double bound were constructed in up to quantitative yields with high stereospecificity.