Lewis acid catalyzed formal [3+2] cycloaddition of donor-acceptor cyclopropanes and 1-Azadienes: synthesis of imine functionalized cyclopentanes and pyrrolidine derivatives

Abstract

Lewis acid catalyzed formal [3+2] cycloadditions of 1-azadienes with donor acceptor cyclopropanes to synthesize varieties of imine functionalized cyclopentanes and pyrrolidine derivatives in moderate to high yield have been developed. Moreover, pharmaceutically relevant azabicyclo[3.2.1] octane, bearing two all-carbon quaternary stereogenic centers at the bridgehead positions, has been synthesized by nosyl group deprotection and intramolecular amidation of imine functionalized cyclopentane derivative.