A refined synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids

作者：Declerck Valerie; Aitken David J^*

来源：Amino Acids, 2011, 41(3): 587-595.

DOI：10.1007/s00726-011-0918-y

• 2-Aminocyclobutanecarboxylic acids
• Photochemical [2+2] cycloaddition
• Chiral resolution
• Epimerization
• Oxazolidin-2-one

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.

• 出版日期2011-8