A novel synthetic method for the preparation of β-keto esters has been developed. α-Phenylseleno acetate was treated with LDA to produce a selenium-stabilised carbanion, which reacted with aldehydes, followed by selenoxide syn-elimination, to give β-keto esters.
(a) BenettiS., RomagnoliR., De RisiC., SpallutoG., and ZaniratoV., Chem. Rev., 1995, 95, 1065; (b) W. Wierenga and H.I. Skulnick, J. Org. Chem., 1979, 44, 310; (c) E.C. Taylor and I.J. Turchi, Org. Prep. Proced. Int., 1978, 10, 221; (d) A. Armati, P. De Ruggeri, E. Rossi and R. Stradi, Synthesis, 1986, 573.
2.
NicolaouK.C., and PetasisN.A., in Selenium in Natural Product Synthesis, CIS, Philadelphia, 1984.
3.
KriefA., Tetrahedron, 1980, 36, 2531.
4.
ChieffiA., and ComassetoJ.V., in Organoselenium Chemistry, BackT.G., Ed.; Oxford University Press: Oxford, 1999; Chapter 7.
5.
(a) QianH., and HuangX., Synlett, 2001, 1571; (b) H. Qian and X. Huang, Tetrahedron Lett., 2002, 43, 1059; (c) H. Qian and X. Huang, J. Comb. Chem., 2003, 5, 569; (d) H. Qian and X. Huang, Synlett, 2006, 1547; (e) H. Qian and X. Huang, Synthesis, 2006, 1934.
6.
ArmaregoW.L.F., and ChaiC.L.L., Purification of Laboratory Chemicals, 5th edn, Butterworth-Heinemann, 2003.
7.
LucchettiL., and KriefA., Tetrahedron Lett., 1978, 19, 2693.
