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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.

SUBMITTER: Lim HJ

PROVIDER: S-EPMC3351792 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Diastereoselective one-pot synthesis of 7- and 8-substituted 5-phenylmorphans.

Lim Hwan Jung HJ Deschamps Jeffrey R JR Jacobson Arthur E AE Rice Kenner C KC

Organic letters 20110912 19

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. ...[more]

PMID: 21905747

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