title: Diastereoselective one-pot synthesis of 7- and 8-substituted 5-phenylmorphans.
abstract: Novel 7- and 8-alkyl and aryl substituted 5-phenylmorphans were synthesized from substituted allyl halides and N-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.
authors: Drug Design and Synthesis Section, CBRB, 5625 Fishers Lane, Room 4N03, National Institute on Drug Abuse, National Institutes of Health, DHHS, Rockville, Maryland 20852, USA.
authors: Hwan Jung
authors: HJ
authors: Lim
authors: Jeffrey R
authors: JR
authors: Deschamps
authors: Arthur E
authors: AE
authors: Jacobson
authors: Kenner C
authors: KC
authors: Rice
mesh_terms: D000478:Alkylation; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D009019:Morphinans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D009019:Morphinans; C042531:phenylmorphan