Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, USA.
Org Lett. 2012 Jul 6;14(13):3404-7. doi: 10.1021/ol3013793. Epub 2012 Jun 18.
(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.
(羟甲基)磷化合物是众所周知的有价值的化合物;然而,(羟甲基)膦酸酯 R(1)P(O)(OR(2))CH(2)OH 的用途却受到了更多的限制。由于无法实现温和脱保护羟甲基基团,因此该功能尚未得到充分利用。本文描述了使用 Corey-Kim 氧化法将 R(1)P(O)(OR(2))CH(2)OH 温和氧化转化为 R(1)P(O)(OR(2))H。还报道了其他保留亚甲基碳的反应。