Chemistry of the versatile (hydroxymethyl)phosphinyl P(O)CH2OH functional group

Org Lett. 2012 Jul 6;14(13):3404-7. doi: 10.1021/ol3013793. Epub 2012 Jun 18.

Abstract

(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.