Diastereo- and Enantioselective Synthesis of (+)- and (−)-cis-2-Aminocyclobutanols

Abstract

The hitherto unknown (+)- and (−)-cis-2-aminocyclobutanols 6a,b and 7a,b, as well as the corresponding benzyloxycyclobutanamines 8a,b, have been synthesized by means of asymmetric reductive amination, with de values of 100% and ee values ranging from 96.9 to 99.8%. The relative cis configuration has been established by NO experiments, whereas the absolute stereochemistry has been deduced from the CD spectra of the corresponding salicylidene derivatives and confirms the like induction at C-1.