Synthesis of enantiopure cyclobutane amino acids and amino alcohols

(−)-(1R,3S)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid and (+)-(1R,3S)-3-amino-2,2-dimethylcyclobutylmethanol, which can be used to prepare enantiopure oligopeptides and cyclobutane-based carbocyclic nucleosides, were synthesized from (+)-(1R)-α-pinene.

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(1R,3S)-3-Amino-2,2-dimethylcyclobutanecarboxylic acidC7H13NO2Ee > 97%[α]D25=-21.5 (c 0.57, MeOH)Source of chirality: Natural chiral poolAbsolute configuration: (1R,3S)

(1R,3S)-3-Amino-2,2-dimethylcyclobutylmethanolC7H15NOEe > 97%[α]D25=+20.6 (c 1.05, MeOH)Source of chirality: Natural chiral poolAbsolute configuration: (1R,3S)