Similar articles

Abstract: A simple and convenient procedure for stereoselective synthesis of (Z)-allyl selenides has been developed by a one-pot reaction of diselenides with baylis-Hillman adducts in the presence of samarium metal-trimethylsilyl chloride under mild conditions. Presumably, the diselenides are cleaved by sm/TMSCl system to form selenide anions, which then undergo S_N2′ substitution of baylis-Hillman adducts to produce the (Z)-allyl selenides.

[1] Back, T.G., Moussa, Z., 2002. Remarkable activity of a novel cyclic seleninate ester as a glutathione peroxidase mimetic and its facile in situ generation from allyl 3-hydroxypropyl selenide. J. Am. Chem. Soc., 124(41):12104-12105.

[2] Back, T.G., Moussa, Z., 2003. Diselenides and allyl selenides as glutathione peroxidase mimetics. Remarkable activity of cyclic seleninates produced in situ by the oxidation of allyl ω-hydroxyalkyl selenides. J. Am. Chem. Soc., 125(44):13455-13460.

[3] Basavaiah, D., Sarma, P.K.S., Bhavani, A.K.D., 1994. Applications of the Baylis-Hillman reaction 2: a simple stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes. J. Chem. Soc., Chem. Commun., (9):1091-1092.

[4] Basavaiah, D., Bhavani, A.K.D., Pandiaraju, S., Sarma, P.K.S., 1995. Baylis-Hillman reaction: magnesium bromide as a stereoselective reagent for the synthesis of [E]- and [Z]-allyl bromides. Synlett., (3):243-244.

[5] Basavaiah, D., Rao, P.D., Hyma, R.S., 1996. The Baylis-Hillman reaction: a novel carbon-carbon bond forming reaction. Tetrahedron, 52(24):8001-8062.

[6] Basavaiah, D., Rao, A.J., Satyanarayana, T., 2003. Recent advances in the Baylis-Hillman reaction and applications. Chem. Rev., 103(3):811-891.

[7] Calò, V., Lopez, L., Pesce, G., 1988. A simple three-step synthesis of β,β-disubstituted acrylates. J. Organomet. Chem., 353(3):405-409.

[8] Carter, R.G., Bourland, T.C., 2000. The first vanadium-catalyzed oxidation of aryl allylic selenides with in situ [2,3] sigmatropic rearrangement. Chem. Commun., (20):2031-2032.

[9] Chavan, S.P., Ethiraj, K.S., Kamat, S.K., 1997. Facile synthesis of 2E-2-chloromethyl aryl-2-enoates. Tetrahedron Lett., 38(42):7415-7416.

[10] Das, B., Mahender, G., Chowdhury, N., Banerjee, J., 2005a. Single-step stereoselective synthesis of (E)- and (Z)-allylamines from acetyl derivatives of Baylis-Hillman adducts. Synlett, (6):1000-1002.

[11] Das, B., Majihi, A., Banerjee, J., Chowdhury, N., Venkateswarlu, K., 2005b. A highly efficient stereoselective synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts. Tetrahedron Lett., 46(46):7913-7915.

[12] Fujita, K., Kanakubo, M., Ushijima, H., Oishi, A., Ikeda, Y., Taguchi, Y., 1998. A symmetric [2,3] sigmatropic rearrangement of opticallyl active allylic selenides. Synlett., (9):987-988.

[13] Hori, T., Sharpless, K.B., 1979. Conversion of allylic phenylselenides to the rearranged allylic chlorides by N-chlorosuccinimide. Mechanism of selenium-catalyzed allylic chlorination of beta-pinene. J. Org. Chem., 44(23):4208.

[14] Huang, Y., Chen, R.Y., 2000. A novel synthesis of allyl selenides by reaction of an organosamarium reagent with alkyl selenocyanates. Synth. Commun., 30(2):377-381.

[15] Janecki, T., Bodalski, R., 1990. A convenient method for the synthesis of substituted 2-methoxycarbonyl- and 2-cyano-allylphosphonates. The allyl phosphite-allyl-phosphonate rearrangement. Synthesis, (9):799-801.

[16] Kabalka, G.W., Venkataiah, B., Dong, G., 2004. Pd-catalyzed cross-coupling of Baylis-Hillman acetate adducts with bis(pinacolato)diboron: an efficient route to functionalized allyl borates. J. Org. Chem., 69(17):5807-5809.

[17] Larson, G.L., de Kaifer, C.F., Seda, R., Terres, L.E., Ramirez, J.R., 1984. A stereoselective, two-step preparation of alpha-alkyl-alpha, beta-unsaturated esters. J. Org. Chem., 49(18):3385-3386.

[18] Liu, Y.K., Li, J., Zheng, H., Xu, D.Q., Xu, Z.Y., 2005. An atom-economical and environmentally benign preparation of unsymmetrical bis-allyl ethers via dimerization of Baylis-Hillman adducts catalyzed by cesium hydroxide monohydrate. Synlett., (19):2999-3001.

[19] Liu, Y.K., Xu, X.S., Zheng, H., Xu, D.Q., Xu, Z.Y., 2006. A facile and stereoselective synthesis of unsymmetrical diallylsulfides via indium-promoted one-pot reaction of Baylis-Hillman acetates, sodium thiosulfate, and allyl bromide. Synlett., (4):571-574.

[20] Lu, G.L., Zhang, Y.M., 1999. Facile formation of samarium(III) selenoates from potassium iodide catalyzed reaction of samarium metal and selenides, and their application in synthesis of selenoesters. Synth. Commun., 29(2):219-225.

[21] Masugama, Y., Yamada, K., Shimizu, S., 1989. Hexacarbonylbdenum(0)-induced dechalcogenization of allylic sulfides, sulfones, and selenides: nucleophilic substitution and reductive dechalcogenization. Bull. Chem. Soc. Jpn., 62(9):2913-2918.

[22] Munbunjong, W., Lee, E.H., Chavasiri, W., Jang, D.O., 2005. Indium-mediated mild and efficient one-pot synthesis of alkyl phenyl selenides. Tetrahedron Lett., 46(50):8769-8771.

[23] Nishiyama, H., Itagaki, K., Osaka, N., Itoh, K., 1982. Transformation of α-phenylseleno ketones to allylic selenides via migration of the phenylseleno group. Tetrahedron Lett., 23(40):4103-4106.

[24] Ranu, B.C., Das, A., 2005. A convenient synthesis of β-phenylselenocarbonyl compounds by in-TMSCl promoted cleavage of diphenyl diselenide and subsequent michael addition. Adv. Synth. Catal., 347(5):712-714.

[25] Roy, O., Riahi, A., Henin, F., Muzart, J., 2000. Synergy or competition between palladium-catalysis and KF/alumina-mediation for the allylic substitution of the acetates of Baylis-Hillman adducts by phenols. Tetrahedron, 56(41):8133.

[26] Sharpless, K.B., Lauer, R.F., 1972. Facile thermal rearrangements of allyl selenides and diselenides [1,3] and [2,3] shifts. J. Org. Chem., 37(24):3973-3974.

[27] Shea, R.G., Fitzner, J., Fankhauser, J.E., Spaltenstein, A., Carpino, P.A., Peevey, R.M., Pratt, D.V., Tenge, B.J., Hopkins, P.B., 1986. Allylic selenides in organic synthesis: new methods for the synthesis of allyl amines. J. Org. Chem., 51(26):5243-5252.

[28] Suzuki, H., Yoshinaga, M., Takaoka, K., Hiroi, Y., 1985. A simple synthesis of aryl difluoromethyl selenides and tellurides. Synthesis, (5):497-499.

[29] Yadav, J.S., Reddy, B.V.S., Madan, C., 2001. Montmorillonite clay-catalyzed stereoselective syntheses of aryl-substituted (E)-and (Z)-allyl iodides and bromides. New J. Chem., 25(9):1114-1117.

[30] Yu, M.X., Zhang, Y.M., Bao, W.L., 1997. The synthesis of allyl selenides by organosamarium reagent. Synth. Commun., 27(4):609-613.

[31] Zhang, Y.M., Yu, Y.P., Lin, R.H., 1993. Cleavage of selenium-selenium and tellurium-tellurium bond by samarium diiodide: synthesis of selenoesters, telluroesters, unsymmetrical alkyl phenyl selenides and tellurides. Synth. Commun., 23(2):189-193.

[32] Zhou, L.H., Zhang, Y.M., 1999. Low-valent titanium induced reductive coupling of diaryl diselenides with acid chlorides or acid anhydrides: facile synthesis of selenoesters. J. Chem. Res., (1):28-29.