Synthesis of highly functionalized β-Aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines

Abstract

A rapid and simple procedure was devised for the synthesis of multifunctionalized cyclic β-amino esters and γ-amino alcohols via the 1,3-dipolar cycloaddition of nitrile oxides to β- aminocyclopentenecarboxylates. The opening of the isoxazoline reductive ring to the corresponding highly functionalized 2-aminocyclopentanecarboxylates occurred stereoselectively with good yields. © 2012 Nonn et al; licensee Beilstein-Institut.