Synthesis of cis-2-fluorocyclopropylamine by stereoselective cyclopropanation under phase-transfer conditions
cis-2-Fluorocyclopropylamine is stereoselectively synthesized by cyclopropanation of 3-aryl-2-vinyl-3-(methoxy)isoin-dol-1-one by treating dibromofluoromethane with saturated aqueous KOH solution in the presence of 18-crown-6 in dichloromethane, followed by removal of a bromine atom of the formed bromofluorocyclopropane derivative with Raney Ni, and successive three steps-deprotection procedures for generating an amino group on the cyclopropane ring.
Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution
The title synthesis was achieved by employing highly cis-selective cyclopropanation of N-benzyl-N-vinylcarbamates with zinc-monofluorocarbenoid, deprotection of the formed N-benzyl-N-(cis-2-fluorocyclopropyl)carbamates, and optical resolution of the resul
Synthesis and optical resolution of dl-cis-2-fluorocyclopropylamine, the key component of the new generation of quinolonecarboxylic acid, DU-6859
The title synthesis was accomplished by featuring highly cis-selective cyclopropanation of an N-vinylcarbamate with zinc-monofluorocarbenoid followed by deprotection of the formed N-(cis-2-fluorocyclopropyl)carbamate. Optical resolution of dl-cis-2-fluoro