Stereoselective synthesis of polyhydroxylated pyrrolidines:a route to novel 3,5-bis(hydroxymethyl)pyrrolidines from 2-azabicyclo[2.2.1]hept-5-enes

摘要

An efficient preparation of racemic and chiral 2-functionalized-3,5-bis(hydroxymethyl)pyrrolidines is described.The method uses 2-azabicyclo[2.2.1]hept-5-enes,readily obtained from glyoxylates of aliphatic amines and cyclopentadiene,as starting material.The hydroxylation of the double bond followed by the oxidative cleavage of the six-membered ring and in situ reduction of the dialdehyde intermediate gives the title pyrrolidines.