Diastereoselective One-Pot Synthesis of 7- and 8-Substituted 5-Phenylmorphans∥Probes for Narcotic Receptor Mediated Phenomena. 45.

Novel 7- and 8-alkyl and aryl substituted 5-phenylmorphans were synthesized from substituted allyl halides and <i>N</i>-benzyl-4-aryl-1,2,3,6-tetrahydropyridine by a highly efficient and diastereoselective reaction series, “one-pot” alkylation and ene-imine cyclization followed by sodium borohydride reduction. Mild cyclization conditions gave the desired substituted 5-phenylmorphans in good yield as a single diastereomer.