Reactivity and synthetic applications of ethyl 4,4-difluoro-3-(triethylsilyl)but-2-enoate

ORGN 113

Masaaki Omote and John T. Welch, Department of Chemistry, University at Albany, 1400 Washington Avenue, Albany, NY 12222
4,4-Difluorobut-2-enoate (2) prepared stereoselectively from 1 is a useful fluorinated building block. Treatment of 2 dissolved in DMSO with KF-H2O or KF-I2 gave 3 or 4, respectively. Synthetically useful diene 5 was available by the deprotonation of 2 with lithium diisopropylamide followed by quenching with TMSCl. The reactivity and synthetic applications of 2, those of 3, 4, 5, will be discussed.