The ring opening reaction of a wide range of mono-, di- and trisubstituted epoxides with the phenylselenide anion under PTC conditions provides a simple, mild and efficient method for preparation of β-hydroxy phenylselenides with high regio- and stereoselectivity in yields from 67 to 98%. The reactions are carried out in aqueous NaOH/ THF using aminoiminomethanesulfinic acid (thiourea dioxide, TDO) to generate sodium phenylselenide from diphenyldiselenide.
ReichH.J., Oxidation in organic chemistry, TrahanovskyW.S., (ed.), Academic Press: New York, Part C, 1978, p. 1.
3.
CareyF.A., and SundbergR.J., Advanced Organic Chemistry, Part A: Structure and Mechanisms, 3rd edn, Plenum Press: New York, 1990, pp 286.
4.
MarchJ., Advanced organic chemistry: reactions, mechanism and structure, 4th edn, Wiley-Interscience: New York, 1992, pp 1022.
5.
PaulmierC., Selenium reagents and intermediates in organic synthesis, Organic Chemistry Series, J.E. Baldwin, (ed), Pergamon: Oxford, New York, 1986, pp. 25–27.
6.
LiottaD., Acct. Chem. Res., 1984, 17, 28.
7.
ReichH.J., Acct. Chem. Res., 1979, 12, 22.
8.
SharplessK.B., and LauerR.F., J. Am. Chem. Soc., 1973, 95, 2696.
9.
SharplessK.B., LauerR.F., and TeranishiA.Y., J. Am. Chem. Soc., 1973, 95, 6137.
10.
LiottaD., MarkiewiczW., and SantiestebanH., Tetrahedron Lett., 1977, 4365.
11.
LeyS.V., O'NeilI.A., and LowC.M.R., Tetrahedron, 1986, 42, 5363.
12.
WeberJ.V., FallerP., KirschG., and SchneiderM., Synthesis, 1984, 1044.
13.
SuzukiH., Yoshinaga, TakaokaM., and HiroiK.Y., Synthesis, 1985, 497.
14.
DowdP., and KennedyP., Synth. Commun., 1981, 11, 935.
15.
ReichH.J., ChowF., and ShahS.K., J. Am. Chem. Soc., 1979, 101, 6638.
16.
GüntherW.H.H., J. Org. Chem., 1966, 31, 1202.
17.
SalmondW.G., BartaM.A., CainA.M., and SobalaM.C., Tetrahedron Lett., 1977, 1683.
