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

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
7
Issue
12
Identifiers
DOI: 10.1016/s0957-4166(96)00454-5

Abstract

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.

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