Stereocontrolled Synthesis of Erythro N-Protected α-Amino Epoxides and Peptidyl Epoxides.

Amnon Albeck, Rachel Persky

Research output: Contribution to journalArticlepeer-review

66 Scopus citations

Abstract

N-protected α-amino epoxides of erythro configuration, derived from α-amino acids, were synthesized in a stereoselective manner. The erythro (2S,3S) configu- ration was achieved by the synthetic sequence: amino acid → haloketone → halohydrin → epoxide. A mechanistic explanation for the observed stereoselectivity is presented. This stereoselective synthetic approach was applied to the synthesis of a variety of short peptidyl epoxides, bearing a predefined absolute configuration of the chiral epoxide moiety.

Original languageEnglish
Pages (from-to)6333-6346
Number of pages14
JournalTetrahedron
Volume50
Issue number21
DOIs
StatePublished - 1994

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