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Synthesis of (+)-(1S,2R) and (−)-(1R,2S)-2-aminocyclobutane-1-carboxylic acids
Authors:Christine Gauzy
Institution:Laboratoire SEESIB-CNRS, Département de Chimie, Université Blaise Pascal, Clermont-Ferrand II, 24 Avenue des Landais, 63177 Aubière cedex, France
Abstract:(+)-(1S,2R) and (−)-(1R,2S)-2-aminocyclobutane-1-carboxylic acids have been prepared in >97% ee and in 33% and 20% overall yields starting from a single, chiral, bicyclic compound perceived as a chiral uracil equivalent. Construction of the cyclobutane ring is achieved via a 2+2] photocycloaddition reaction of this chiral precursor with ethylene.
Keywords:β-Amino acid  Cyclobutane  Stereoselective synthesis  [2+2] Photocycloaddition reaction
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