Evaluation of an Aza-Michael approach for the synthesis of 3,3-dimethyl-2-aminocyclobutane-1-carboxylic acid
Résumé
The aza-Michael addition reaction of a dibenzylic amide anion with t-butyl 3,3-dimethylcyclobutene-1-carboxylate was investigated as a route to the title compound, a cyclic β-amino acid. In analogy with the known 5- and 6-membered ring homologues, the addition reaction proceeds smoothly, but with moderate diastereomeric and enantiomeric selectivities. The trans isomer of the title β-amino acid was obtained, for the first time, with a modest enantiomeric excess