Stereoselective synthesis of fluorinated beta-aminoacids from ethyl trans-N-benzyl-3-trifluoromethylaziridine-2-carboxylate

trans-N-Benzyl-3-trifluoromethyl-2-ethoxycarbonylaziridine 2a, easily obtai nable in enantiopure forms by CAL-catalysed enzymatic resolution, allowed t he regio- and stereoselective synthesis of chiral fluorinated anti-alpha-fu nctionalised-beta-aminoacids, such as trifluoroisoserinates or trifluoro-be ta-alanine, and trans-3-halo- or 3-hydroxy-beta-lactams. Starting from the enantiomerically pure methyl analogue of the title compound, 2c, pure enant iomers of trifluoroisoserine can be obtained in high overall chemical yield . Absolute configurations of optically active beta-aminoacids were determin ed by chemical correlation. (C) 1999 Elsevier Science Ltd. All rights reser ved.