Chemistry of the versatile (hydroxymethyl)phosphinyl P(O)CH2OH functional group.
(Hydroxymethyl)phosphorus compounds are well-known and valuable compounds in general; however the use of (hydroxymethyl)phosphinates R(1)P(O)(OR(2))CH(2)OH in particular has been much more limited. The potential of this functionality has not yet been fully realized because the mild unmasking of the hydroxymethyl group was not available. The mild oxidative conversion of R(1)P(O)(OR(2))CH(2)OH into R(1)P(O)(OR(2))H using the Corey-Kim oxidation is described. Other reactions preserving the methylene carbon are also reported.
Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, USA.
Olivier
O
Berger
Laurent
L
Gavara
Jean-Luc
JL
Montchamp