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Radical reactions leading to substituted pyroglutamates

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
18
Identifiers
DOI: 10.1016/s0040-4039(98)00254-8

Abstract

Abstract The Bu 3SnH mediated cyclisation of a serine-derived dehydroalanine was shown to provide an efficient approach to a protected 4-phenylpyroglutamate which was elaborated to 4-phenylglutamic acid in good yield. Cyclisation reactions of this type were shown to proceed via an intermediate captodative radical which could be trapped intermolecularly using an alkene e.g. styrene or methyl methacrylate. This method has potential for the synthesis of various 4- and/or 2-substituted glutamic acids.

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