Work

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

Year: 2011

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol2021862

Authors: Hwan Jung Lim, Jeffrey R. Deschamps, Arthur E. Jacobson, Kenner C. Rice

Institutions: United States Naval Research Laboratory, National Institutes of Health, National Institute on Drug Abuse, National Institute on Alcohol Abuse and Alcoholism

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute on Alcohol Abuse and Alcoholism, National Institute on Drug Abuse, National Institute of Diabetes and Digestive and Kidney Diseases

Awards: G3883660972, BRIDGING THE DISCONNECT, G9000110550