Studies on the aza-Claisen rearrangement of 4,5-dihydroxylated allylic trichloroacetimidates: the stereoselective synthesis of (2R,3S)- and (2S,3S)-2-amino-3,4-dihydroxybutyric acids

Swift, M. D. and Sutherland, A. (2008) Studies on the aza-Claisen rearrangement of 4,5-dihydroxylated allylic trichloroacetimidates: the stereoselective synthesis of (2R,3S)- and (2S,3S)-2-amino-3,4-dihydroxybutyric acids. Tetrahedron, 64(40), pp. 9521-9527. (doi: 10.1016/j.tet.2008.07.062)

Abstract

Two new synthetic approaches, involving substrate directed aza-Claisen rearrangements and aza-Claisen rearrangements mediated by chiral Pd(II) catalysts, have been developed for the stereoselective synthesis of (2R,3S)-2-amino-3,4-dihydroxybutyric acid, a dihydroxylated alpha-amino acid from the edible mushroom, Lyophyllum ulmarium and its (2S,3S)-unnatural diastereomer..

• Item Type: Articles
• Keywords: ACID ACIDS AMIDES Amino acids AMINO-ACID AZA-CLAISEN REARRANGEMENT Aza-Claisen rearrangements CATALYST CATALYSTS CATALYTIC ASYMMETRIC REARRANGEMENT Chiral COMPLEXES DERIVATIVES directing effect EDIBLE MUSHROOM ENANTIOSELECTIVE CATALYSTS LYOPHYLLUM-ULMARIUM MODEL PALLADACYCLE CATALYSTS Palladium catalysis rearrangement Stereoselective synthesis STEREOSELECTIVE-SYNTHESIS
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew
• Authors: Swift, M. D., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron
• ISSN: 0040-4020