Enantioselective synthesis of novel homochiral α-substituted (S)-isoserine derivatives. Incorporation of this amino acid in a highly conformationally constrained dipeptide surrogate

Miguel Díaz, Rosa M. Ortuño

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16 Citations (Scopus)

Abstract

Optically pure isoserine derivatives with a chiral polyfunctional bicyclo[3.1.0]hexyl substituent at the α-carboxyl position were synthesized from a common cyclopentene precursor bearing an α-epoxy ester function in a side-chain. Cyclopropanation of the double bond and nucleophilic oxirane-ring opening by using a homochiral amine were the key steps. One of the synthesized derivatives was condensed with Cbz-cyclo-Asp-OMe affording a highly conformationally constrained dipeptide surrogate.
Original languageEnglish
Pages (from-to)3465-3478
JournalTetrahedron Asymmetry
Volume7
Issue number12
DOIs
Publication statusPublished - 1 Dec 1996

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