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

We have disclosed a Rauhut-Currier reaction of & gamma;-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. We have disclosed a Rauhut-Currier reaction of & gamma;-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.

Automated summary

We have revealed a Rauhut-Currier reaction of γ-alkyl-substituted allenoate catalyzed by l-valine-derived amide phosphine to generate trisubstituted allenoate, which then undergoes a Diels-Alder reaction with maleimide or DMAD. The reaction achieves the construction of exo-bicyclic succinimide derivatives with three consecutive stereocenters and an exo-carbon-carbon double bond in high stereospecificity and almost quantitative yields.