C. Doucet, I. Vergely, M. Reboud-Ravaux
Mar 13, 1997
Citations
0
Influential Citations
14
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract (3R)- and (3S)-N-(2-chloromethylphenyl)-3-bromo-3-fluoroazetidin-2-ones 2 were synthesized via the separation of diastereoisomeric phenylglycinol derivatives of the starting 2,3-dibromo-2-fluoropropanoic acid. Acidic hydrolysis of the hydroxyamides led to the chiral trihalogenopropanoic acids. Then, an expeditious four step synthesis provided the (3S)- and (3R)-azetidinones 2, both of which behaved as strictly irreversible inhibitors of HLE. The configuration of the bromofluorocarbon was shown to have a significant effect on the partition ratio: kcat/kinact=4.6 and 34.3 for (3S)- and 3R)-2, respectively.