Development of a new strategy for the synthesis of piperidine and pyrrolidine alkaloids

Abstract

Cyclofunctionalization of N-acyl-O-homoallyl hydroxylamines using palladium(II)chloride as a catalyst in the presence of copper(II) salts, carbon monoxide and methanol gives isoxazolidine products. When the nigrogen is protected as a carbamate, the products are obtained exclusively as their cis-isomer. Catalytic hydrogenation of the benzyloxy carbonyl protected isoxazolidine yields syn-1,3-amino alcohols, the valuable intermediates for the synthesis of many pyrrolidine and piperidine natural products.