Iodine assisted palladium catalyzed ring opening of bicyclic hydrazines with organoboronic acids: Sereoselective synthesis of functionalized cyclopentenes and alkylidene cyclopentenes

Abstract

A Novel reactivity of organoboronic acids with bicyclic hydrazines leading to the stereoselective formation of trans-vicinal disubstituted cyclopentenes in good to excellent yield is discussed. The reaction of cyclopentadiene and fulvene derived azabicyclic alkenenes with organoboronic acids afforded the trans-3,4-disubstituted cyclopentenes and alkylidene cyclopentenes in good to excellent yields. The products, having a broad range of substituents, are important intermediated in the synthesis of a number of pharmaceutically important molecules.