ChemInform Abstract: Synthesis of Pyrrolidine Derivatives by Improved Aminoselenation via Addition of Boron Trifluoride Complex of Dihomoallylcuprate to Aldimines Containing α-Hydrogen.

ChemInform Abstract

The unsaturated amines (III) derived from the imines (I) are cyclized and selenenylated to give the phenylselenenylmethylpyrrolidines (V) which are reduced, forming the methylpyrrolidines (VI). Starting with the magnesium cuprate (VII), the acyclic amine (VIII) is obtained instead of the piperidine expected. Subsequent hydrolysis or oxidative elimination yields the alcohol (IX) and the vinyl chloride (X). Addition of (VII) to (Ia) followed by cyclization produces the piperidine (XI).