One-pot Synthesis of Vinyl Phosphonates from 2-hydroxyalkyl Phenyl Selenides with Monoethyl Esters of Phosphonic Acid

(a) Kosolapoff G.M. , and Maier L. , (ed), Organic phosphorus compounds; Wiley-Interscience: New York, 1972; (b) D.E.C. Corbridge, Phosphorus: an outline of its chemistry, biochemistry and uses, 5thed.; Elsevier: Amsterdam; 1995.

Engel R. , In Handbook of Organophosphorus Chemistry, Marcel Dekker: New York, 1992.

(a) Hang S.B. , Mullins T.S. , Shim H. , and Raushal F.M. , Biochemistry, 1997, 36, 9022; (b) M.M. Berggren, L.A. Burns, R.T. Abraham, G. Powis, Cancer Res., 1993, 53, 1862; (c) X.D. Cao, E.J. Moran, D. Siev, A. Lio, C. Ohashi and A.M.M. Mjalli, Bioorg. Med. Chem. Lett., 1995, 5, 2953; (d) A. Caseli, G. Ciamici, G. Manao, G. Moneti, L. Pazzagli, G. Cappugi and G. Rammponi, J. Biol. Chem., 1994, 269, 24878.

(a) Stowell J.K. , and Widlanski T.S. , J. Org. Chem., 1995, 60, 6930; (b) J.K. Myers, J.D. Cohen and T.S. Widlanski, J. Am. Chem. Soc., 1995, 117, 11049.; (c) T.S. Widlanski, J.K. Myer, B. Stec, K.M. Holtz and E.R. Kantroewitz, Chem. Biol. 1997, 4, 489.

Maurer F. , Riebel H.J. , Hammann I. , Behrenz W. , and Homeyer B. , Ger. Offen. 2533601, 1977; Chem. Abstr., 1977, 87, 17324.

Molodykh Z.V. , Aleksandrova I.A. , Belyalov R.U. , Gazizor T.K. , and Reznik V.S. , Khim.-Farm. Zh., 1990, 24, 136. Chem. Abstr., 1990, 113, 20789.

Despax C. , and Navech J. , Tetrahedron Lett., 1990, 31, 4471.

Trishin Yu G. , Burangulova R.N. , Konovalova I.V. , Burnaeva L.A. , and Akimova G.S. , Dokl. Akad. Nauk., 1989, 304, 625; Chem. Abstr., 1990, 112, 35988.

(a) Wasserman H.H. , and Cohen D. , J. Am. Chem. Soc., 1960, 82, 4435; (b) H.H. Wasserman and D. Cohen, J. Org. Chem., 1964, 29, 1817.

Hua R. , and Tanaka M. , Chem. Lett., 1998, 431.

Peng A.-Y. , and Ding Y.-X. , Synthesis, 2003, 205.

(a) Reich H.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) Paulmier C. , Ed.; Selenium Reagents and Intermediates in Organic Synthesis, Pergamon Press: Oxford, 1986; (e) T.G. Back, Organoselenium Chemistry, Oxford University Press: Oxford, 1999; (f) T. Wirth, Organoselenium Chemistry, Springer: Berlin, 2000.

For some recent selected examples on organoselenium, see: (a) Devan N. , Sirdhar P.R. , Prabhu K.R. , and Chandrasekaran S. , J. Org. Chem., 2002, 67, 9417; (b) S.S. Khokhar and T. Wirth, Angew. Chem., Int. Ed., 2004, 43, 631; (c) G. Pandey and S.R. Gadre, Acc. Chem. Res., 2004, 37, 201.

(a) Bartlett P.A. , and Chouinard P.M. , J. Org. Chem., 1983, 48, 3854; (b) T.-Q. Chen and M.M. Greenberg, J. Am. Chem. Soc., 1998, 120, 3815.

Krief A. , Tetrahedron, 1980, 36, 2531.

For some recent selected examples for preparation of tetrahydrofuran derivatives using phenyl β-hydroxyalkyl selenides, see: (a) Berlin S. , Ericsson C. , and Engman L. , J. Org. Chem. 2003, 68, 8386; (b) M. Tiecco, L. Testaferri, L. Bagnoli, V. Purgatorio, A. Temperini, F. Marini and C. Santi, Tetrahedron: Asymm., 2004, 15, 405.

For some recent selected examples, seen: (a) Rigby J.H. , Maharoof U.S.M. , and Mateo M.E. , J. Am. Chem. Soc., 2000, 122, 6624; (b) H. Azuma, S. Tamagaki and K. Ogino, J. Org. Chem., 2000, 65, 3538; (c) T.D. Bagul, G. Lakshmaiah, T. Kawabata and K. Fuji, Org. Lett., 2002, 4, 249.

Mitsunobu O. , Synthesis, 1981, 1.

(a) Sheng S.-R. , Liu X.-L. , Xu Q. , and Song C.-S. , Synthesis, 2003, 2763; (b) S.-R. Sheng, X.-L. Liu, X.-C. Wang, Q. Xin and C.-S. Song, Synthesis 2004, 2833; (c) X.-L. Liu, S.-R. Sheng, Q.-Y. Wang, W.-K. Sun, Q. Xin and H.-Y. Ao, J. Chem. Res(S). 2006, 118.

(a) Gnther W.H.H. , J. Org. Chem., 1966, 31, 1202; (b) K.B. Sharpless and R.F. Lauer, J. Am. Chem. Soc., 1972, 94, 5115; (c) J. Remion, W. Dumont and A. Krief, Tetrahedron Lett., 1976, 17, 1385; (d) L. Engman and V. Gupta, J. Org. Chem., 1997, 62, 157.

Rabinowitz R. , J. Am. Chem. Soc., 1960, 82, 4564.

Saunders B.C. , Stacey G.J. , Wild F. , and Wilding I.G.E. , J. Chem. Soc., 1948, 699.

(a) Tavs P. , Chem. Ber., 1970, 103, 2428; (b) R.C. Grabiak, J.A. Miles and G.M. Schwenzer, Phosphorus Sulfur Relat. Elem., 1980, 9, 197.

Hirao T. , Masunaga T. , Ohshiro Y. , and Agawa T. , Synthesis, 1981, 56.