Journal
AMINO ACIDS
Volume 41, Issue 3, Pages 587-595Publisher
SPRINGER WIEN
DOI: 10.1007/s00726-011-0918-y
Keywords
2-Aminocyclobutanecarboxylic acids; Photochemical [2+2] cycloaddition; Chiral resolution; Epimerization; Oxazolidin-2-one
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The synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids has been refined to improve both the efficiency and the simplicity. These improvements provide a shorter and easier access to the racemic cis-cyclobutane beta-amino acid core. Derivatization of this material with a chiral non-racemic oxazolidin-2-one allows easy diastereoisomeric separation and presents the advantage of allowing the non-destructive cleavage of the chiral auxiliary either by hydrolysis or by ammonolysis, thus providing an efficacious access to N-protected derivatives of all four stereoisomers of Boc-2-aminocyclobutanecarboxylic acid.
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