Reactions of fluorinated hydroxy and epoxy ketones with tris(trimethylsilyl) phosphite

Reacting the fluoroalkyl beta-trimethylsiloxy ketones (RC)-C-F(OSiMe3)CH2C( :O)R (R-F = CF3, R = Ph, R-F = C6F13. R= Me) with tris(trimethylsilyl) phos phite gave a diastereomeric mixture of alpha,gamma-hydroxy, phosphonic acid s and their derivatives. With a fluorinated beta-epoxy ketone and tris(trim ethylsilyl) phosphite, corresponding silyl esters and, after hydrolysis, an alpha-hydroxy-beta-epoxy phosphonic acid weve obtained as two diastereomer s. The molecular structure of the latter compound (triclinic P 1 with a = 5 79.30(10), b = 1291.8(2), c = 1630.3(2) pm, alpha = 72.73(1)degrees beta = 87.97(1)degrees, gamma = 86.33(1)degrees Z = 4) was determined exhibiting t wo independent molecules with (RRR) configuration and strong intra and inte rmolecular hydrogen bridges. (C) 1999 John Wiley & Sons, Inc.