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

Authors
  • Berger, Olivier
  • Gavara, Laurent
  • Montchamp, Jean-Luc
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jul 06, 2012
Volume
14
Issue
13
Pages
3404–3407
Identifiers
DOI: 10.1021/ol3013793
PMID: 22708634
Source
Medline
License
Unknown

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.

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