Phosphine-Catalyzed Addition/Cycloaddtion Domino Reaction Of β’-Acetoxy Allenoate

This thesis focuses on the phosphine-catalyzed domino reaction. Two classes of phosphine-catalyzed addition/cycloaddition domino reactions of β’-acetoxy allenoate have been developed. The reaction of β’-acetoxy allenoate with 2-acyl-3-methyl-acrylonitrile readily occurs to give 2-oxabicyclo[33.1]nonane, furnishing the β’-addition/[4+4] cycloaddition domino sequence. In this sequence, P’C of allenoate is an electrophilic center and its β’C and γC serve as 1,4-dipole. When the other reaction partner is switched to 2-acyl-3-(2-pyrrole)-acrylonitrile, γ-addition/[3+2] cycloaddition domino reaction is instead observed delivering the cyclopental-[a]pyrrolizine skeleton, in which allenoate exhibits dual electrophilic reactivity of γC and 1,3-dipole chemical behavior of βC and β’C.This study has not only extended the existing phosphne-catalyzed cycloaddition scope, but also provided a facile access to complex structures.