Rh2(esp)2-catalyzed three-component reaction of a diazo compound, alkyl azide and allylboronate for the synthesis of homoallylic amine derivatives

Abstract

The three-component reaction of a diazo compound, azide and allylboronate was explored, and Rh₂(esp)₂ was utilized as the optimal catalyst. A series of α-amino esters were efficiently produced from the ethyl diazoacetate in 57–84% yields, and excellent diastereoselectivities were observed with the reaction employing (E)-allylboronate as the alkylation reagent. The α-amino ketone or homoallylic amine could also be prepared by using α-diazo ketone or trimethylsilyl diazomethane in acceptable yields.