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A photochemical approach to phenylalanines and related compounds by alkylation of glycine

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JournalTetrahedron
DatePublished - 17 Sep 2001
Issue number38
Volume57
Number of pages10
Pages (from-to)8115-8124
Original languageEnglish

Abstract

Phenylalanines can be prepared on UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, substituted toluenes and the photosensitiser benzophenone. These reactions, which lead to highly selective mono-alkylation at the alpha -position of glycines, involve coupling of captodative alpha -glycine radicals with benzyl radicals. This method can be used to selectively alkylate a variety of glycine derivatives using a range of substituted toluenes under neutral reaction conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

    Research areas

  • alkylation, amino acids and derivatives, photochemistry, radicals and radical reactions, ALPHA-AMINO-ACIDS, FREE-RADICAL REACTIONS, ASYMMETRIC-SYNTHESIS, DERIVATIVES, PHOTOALKYLATION, DESULFONYLATION, HYDROGENATION, CATALYSTS, RESIDUES, ALCOHOLS

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