Microwave-assisted hydrophosphonylation of aldehydes under solvent-free conditions was found to be an efficient method for the preparation of α-hydroxyphosphonates; the method was reliable, efficient and high yielding.
For leading ref. see The Role of Phosphonates in living systems, ed. HildebrandR.L., CRC Press, Boca Raton, Fl., 1983. EngelR., in Organic Reactions, Vol. 36, p. 175, John Wiley & Sons, New York, 1988. KosolapoffM.G., in Organic Reactions, Vol. 6, p. 273, John Wiley & Sons, New York, 1951.
2.
(a) KafarskiP., LejezakB., and MastalerzP., Phosphonopeptides Synthesis, and Biological activity. Beitr. Wirkstofforsch; 1985, Vol. 25, and references cited therein
3.
WangJ.C-L., TaylorL.T., MicalJ.A., SpitzS., and ReillyT., Tetrahedron Lett.1992, 33, 7667
4.
YuanC., and ChenS., Synthesis1992, 1124
5.
PeymanA., BudtK-H., SpanigJ., StowasserB., and RuppertD., Tetrahedron Lett.1992, 33, 4549
6.
SorokaM., Liebigs Ann. Chem.1990, 331
7.
BartlettP., and GiannousisP.P., J. Med. Chem.1987, 30, 1603.
8.
(a) PatelD.V., Rielly-GauvinK., and RyonoD.E., Tetraheron Lett.1990, 31, 5587
9.
PatelD.V., Rially-gauvinK., and RyonoD.E., Tetrahedron Lett.1990, 31, 5591.
StowasserB., BudtK-H., Jian-QiL., PeymanA., and RuppertD., Tetrahedron Lett.1989, 33, 6625.
12.
BurkeT.R.Jr., LiZ.-H., BolenJ.B., and MarquezV.E., J. Med. Chem., 1991, 34, 1577.
13.
HammerschmidtF., and VollenkleH., Liebigs Ann. Chem.1989, 577; YokomatsuT., and ShibuyaS., Tetrahedron: Asymmetry, 1992, 3, 377; BaraldiP.G., GuarneriM., MoroderF., PolliniG.P., and SimoniD., Synthesis 1982, 653; MaierL., Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76, 379.
14.
OhlerE., and KotzingerS., Synthesis1993, 497–502, and references cited terein. For a review see: KafarskiP., LejczakB., Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193.
15.
(a) PudovikA.N., Dokl. Akad. Nauk SSSR1950, 73, 499; C. A. 1951, 45, 2856. b) BlazisV.J., KoellerK.J., and SpillingC.D., Tetrahedron: Asymmetry, 1994, 5, 499, and references therein.
16.
(a) FadelA., YefashR., and SaluanJ., Synthesis, 1987, 37
17.
RosiniG., GalariniR., MarottaE., and RighiR., J. Org. Chem., 1990, 55, 781
18.
KodomariM., SakamotoT., and YoshitomiS., J. Chem. Soc. Chem. Cummun.1990, 701
19.
KroppP.J., DausK.A., CrawfordS.D., TubergrenM.W., KeplerK.D., CraigS.L., and VilsonV.P., J. Am. Chem. Soc.1990, 112, 7433