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

✍ Scribed by Vitalij G. Ratner; Enno Lork; Kazimir I. Pashkevich; Gerd-Volker Röschenthaler

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 172 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:7<632::aid-hc18>3.0.co;2-n

✦ Synopsis

Reacting the fluoroalkyl b-trimethylsi-

R‫ס‬ Me) with tris(trimethylsilyl) phosphite gave a diastereomeric mixture of ␣,c-hydroxy phosphonic acids and their derivatives. With a fluorinated b-epoxy ketone and tris(trimethylsilyl) phosphite, corresponding silyl esters and, after hydrolysis, an ␣-hydroxy-b-epoxy phosphonic acid were obtained as two diastereomers. The molecular structure of the latter compound (triclinic P 1 ¯with a ‫ס‬ 579.30 (10), b ‫ס‬ 1291.8(2), c ‫ס‬ 1630.3(2) pm, ␣ ‫ס‬ 72.73(1)Њ, b ‫ס‬ 87.97(1)Њ, c ‫ס‬ 86.33(1)Њ, Z ‫ס‬ 4) was determined, exhibiting two independent molecules with (RRR) configuration and strong intra and intermolecular hydrogen bridges.