Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

P. E. Maligres, S. A. Weissman, V. Upadhyay, S. J. Cianciosi, R. A. Reamer, R. M. Purick, J. Sager, K. Rossen, K. K. Eng, D. Askin, R. P. Volante, P. J. Reider

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

Reaction of 2-alkyl-4-enamides with I+ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).

Original languageEnglish (US)
Pages (from-to)3327-3338
Number of pages12
JournalTetrahedron
Volume52
Issue number9
DOIs
StatePublished - Feb 26 1996
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • enamide
  • epoxidation
  • imidate
  • indinavir
  • iodohydrin

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