Treatment of lithio derivatives of polystyrene-supported methyl α-selenopropionate, 2-selenopropiophenone, 1-selenoethyl phenyl sulfone and diethyl 1-selenoethylphosphonate with aldehydes respectively, followed by cleavage from the polymer by oxidation-elimination with 30% hydrogen peroxide efficiently afforded Baylis–Hillman products in good yields and high purities.
Recent reviews on SPOS. (a) GuillierF., OrainD., and BradleyM., Chem. Rev., 2000, 100, 2091; (b) R.E. Sammelson and M.J. Kurth, Chem. Rev., 2001, 101, 137; (c) A.W. Czarnik, Solid-phase organic synthesis; Wiley: New York, 2001; Vol. 1; (d) K.C. Nicolaou, R. Hanko and H. Hartwig, Handbook of Combinatorial Chemistry; Wiley-VCH: Weinheim, Germany, 2002; (e) R.E. Dolle, J. Comb. Chem., 2002, 4, 369; (f) W. Bannwarth, In Combinatorial Chemistry: A Practical Approach; BannwarthW., and FelderE., Ed.; Wiley-VCH: Weinheim, 2000; pp. 47-95 and references cited therein.
2.
For review, see: (a) DrewesS.E., and RoosG.H.P., Tetrahedron, 1988, 44, 4653; (b) D. Basavaiah, P.D. Rao and R.S. Hyma, Tetrahedron, 1996, 52, 8001; (c) E. Ciganek, Org. React., 1997, 51, 201; (d) I.E. Marko, G.P. Giles and N.J. Hindley, Tetrahedron, 1997, 53, 1015; (e) P. Langer, Angew. Chew., Int. Ed., 2000, 39, 3049; (f) D. Basavaiah, A.J. Rao and T. Satyanarayana, Chem. Rev., 2003, 103, 811.
3.
For some recent examples for preparation of Baylis–Hillman adducts, see: (a) de SouzaR.O.M.A., MeirelesB.A., AguiarL.C.S., and VasconcellosM.L.A.A., Synthesis, 2004, 1595; (b) P.R. Krishna, E.R. Sekhar and S.V. Kannan, Synthesis, 2004, 857; (c) L.-J. Zhao, H.S. He, M. Shi and P.H. Toy, J. Comb. Chem., 2004, 6, 680; (d) S.Z. Luo, P.G. Wang and J.-P. Cheng, J. Org. Chem., 2004, 69, 555; (d) P.R. Krishna, K.R. Lopinti and V. Kannan, Tetrahedron Lett., 2004, 45, 7847; (e) P.R. Krishna, A. Manjuvani, V. Kannan and G.V.M. Sharma, Tetrahedron Lett., 2004, 45, 1183; (f) X.L. Mi, S.Z. Luo and J.-P. Cheng, J. Org. Chem., 2005, 70, 2338; (g) P. Caumul and H.C. Hailes, Tetrahedron Lett., 2005, 46, 8125; (h) S.I. Pereira, J. Adrio, A.M.S. Silva and J.C. Carretero, J. Org. Chem., 2005, 70, 10175; (i) S. Xue, L. He, K.-Z. Han, Y.-K. Liu and Q.-X. Guo, Synlett, 2005, 1247; (j) P.R. Krishna, A. Manjuvani, and E.P. Sekhar, Arkivoc, 2005, 99; (k) Y.-S. Lin, C.-Y. Lin, C.-E. Liu and T.Y. R. Tsai, Tetrahedron, 2006, 62, 872.
4.
(a) ReichH.J., Acc. Chem. Res., 1979, 12, 22; (b) D. Liotta, Acc. Chem. Res., 1984, 17, 28; (c) K.C. Nicolaou and N.A. Petasis, Selenium in Natural Product Synthesis, CIS: Philadelphia, 1984; (d) PaulmierC., Ed. Selenium Reagents and Intermediates in Organic Synthesis, Pergamon Press: Oxford, 1986; (e) D. Liotta, Ed. Organoselenium Chemistry, Wiley: New York, 1987; (f) A. Krief, Comprehensive Organic Synthesis, Pergamon: Oxford, 1991; (g) T.G. Back, Organoselenium Chemistry, Oxford University Press: Oxford, 1999; pp 173-191; (h) T. Wirth, Organoselenium Chemistry, Springer: Berlin, 2000.
5.
RollinsonS.W., AmosR.A., and KatzenellenbogenJ.A., J. Am. Chem. Soc., 1981, 103, 4114.
6.
(a) NicolaouK.C., PastorJ., BarluengaS., and WinssingerN., Chem. Commun., 1998, 1947; (b) T. Ruhland, K. Andersen and H. Pedersen, J. Org. Chem., 1998, 63, 9204; (c) L. Uehlin and T. Wirth, Org. Lett., 2001, 3, 2931; (d) K.-I. Fujita, S. Hashimoto, A. Oishi and Y. Taguchi, Tetrahedron Lett., 2003, 44, 3793; (e) S. Berlin, C. Ericsson and L. Engman, J. Org. Chem., 2003, 68, 8386; (f) R.J. Cohen, D.L. Fox and R.N. Salvatore, J. Org. Chem., 2004, 69, 4265.
7.
(a) HuangX., and ShengS.-R., Tetrahedron Lett., 2001, 42, 9035; (b) X. Huang and S.-R. Sheng, J. Comb. Chem., 2003, 5, 273; (c) X. Huang and W.-M. Xu, Tetrahedron Lett., 2002, 43, 5495; (d) S.-R. Sheng, X.-L. Liu, X.-C. Wang, Q. Xin and C.-S. Song, Synthesis, 2004, 2833; (e) X.-L. Liu, S.-R. Sheng, Q.-Y, Wang, W.-K. Sun, Q. Xin and H.-Y. Ao, J. Chem. Res. 2006, 118.
