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 |
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| Authors: | Michael D Swift |
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| Institution: | WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK |
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| 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 α-amino acid from the edible mushroom, Lyophyllum ulmarium and its (2S,3S)-unnatural diastereomer. |
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| Keywords: | Palladium catalysis Aza-Claisen rearrangement Directing effect Amino acids |
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