Powiadomienia systemowe
- Sesja wygasła!
- Sesja wygasła!
Tytuł artykułu
Autorzy
Wybrane pełne teksty z tego czasopisma
Identyfikatory
Warianty tytułu
The synthesis and reactivity of phosphinous acid-boranes
Języki publikacji
Abstrakty
Borane complexes of trivalent phosphorus compounds are versatile synthetic intermediates which are especially useful in the elaboration of phosphine structures and in the preparation of chiral phosphine ligands. Despite the synthetic importance and wide use of derivatives of phosphinous acid-boranes such as their esters (phosphinite-boranes), or acid chlorides (.sec-chlorophosphine-boranes), the parent phosphinous acid-boranes have until very recently remained practically unexplored. New developments of convenient and general methods of synthesis of phosphinous acid-boranes from secondary phosphine oxides or from phosphinic chlorides have made them now readily accessible as a novel class of organophosphorus reagents. When nonsymmetrically substituted phosphinous acid-boranes bear a center of chirality at P and are configurationally stable. Phosphinous acid-boranes possess a rich reactivity pattern offering many useful synthetic transformations through the reactions at their R, O, or B, reactivity centers. A large variety of other organophosphorus compounds such as phosphinite-boranes, boranatophosphinous anhydrides and mixed anhydrides, secondary phosphine-boranes, tertiary phosphine-boranes, secondary phosphine oxides, phosphinic halides, and oxaphosphaborolidines, can all be readily derived from phosphinous acid-boranes in a single synthetic operation.
Wydawca
Czasopismo
Rocznik
Tom
Strony
323--343
Opis fizyczny
wykr., bibliogr. 23 poz.
Twórcy
autor
autor
- Zakład Chemii Organicznej, Wydział Chemii, Uniwersytet Marii Curie-Skłodowskiej, ul. Gliniana 33, 20-614 Lublin
Bibliografia
- [1] (a) C. Bauduin, D. Moulin, E.B. Kaloun, C. Darcel, S. Jugé, J. Org. Chem., 2003, 68, 4293; (b) H. Lam, D.J. Aldous, K.K. Hii, Tetrahedron Lett., 2003, 44, 5213; (c) D. Moulin, S. Bago, C. Bauduin, C. Darcel, S. Jugé, Tetrahedron: Asymmetry, 2000, 11, 3939; (d) Moulin D., Darcel C., Jugé S., Tetrahedron: Asymmetry, 1999, 10, 4729.
- [2] (a) T. Imamoto, T. Oshiki, T. Onozawa, T. Kusumoto, K. Sato, J. Am. Chem. Soc., 1990, 112, 5244; (b) T. Osiki, T. Imamoto, Bull. Chem. Soc. Jpn, 1990, 63, 3719; (c) T. Osiki, T. Hikosaka, T. Imamoto, Tetrahedron Lett., 1991, 32, 3371; (d) T. Oshiki, T. Imamoto, J. Am. Chem. Soc., 1992, 114, 3975; (e) T. Imamoto, Pure Appl. Chem., 1993, 65, 655; (f) K.M. Pietrusiewicz, M. Zabłocka, Chem. Rev., 1994, 94, 1375; (g) T. Imamoto, H. Tsuruta, Y. Wada, H. Masuda, Yamaguchi K., Tetrahedron Lett., 1995, 36, 8271; (h) Imamoto T., Tsuruta H., Chem. Lett., 1996, 707; (i) U. Nettekoven, M. Widhalm, P.C.J. Kamer, P.W.N.M. van Leeuwen, Tetrahedron: Asymmetry, 1997, 8, 3185; (j) T. Miura, H. Hamada, S. Kikuchi, T. Imamoto, J. Org. Chem., 2000, 65, 1877; (k) H. Tsuruta, T. Imamoto, Synlett, 2001, 999; (l) A. Monsees, S. Laschat, Synlett, 2002, 1011; (m) D. Hobuß, C. Thöne, S. Laschat, A. Baro, Synthesis, 2003, 2053; (n) G. Hoge, J. Am. Chem. Soc., 2003, 125, 10219.
- [3] H. Schmidbaur, J. Organomet. Chem., 1980, 200, 287.
- [4] R. Köster, Y.-H. Tsay, L. Synoradzki, Chem. Ber., 1987, 120, 1117.
- [5] J. Uziel, M. Stephan, E.B. Kaloun, J.P. Genet, S. Jugé, Bull. Soc. Chim. Fr., 1997, 134, 379.
- [6] K. Nagata, S. Matsukawa, T. Imamoto, J. Org. Chem., 2000, 65, 4185.
- [7] T. Imamoto, E. Nagato, Y. Wada, H. Maruda, K. Yamaguchi, T. Uchimaru, J. Am. Chem. Soc., 1997, 119, 9925.
- [8] (a) T. Wada, M. Shimizu, N. Oka, K. Sago, Tetrahedron Lett., 2002, 43, 4137; (b) M. Shimizu, K. Tamura, T. Wada, K. Sago Tetrahedron Lett., 2004, 45, 371.
- [9] (a) J. Zhang, T. Terhorst, M.D. Matteucci, Tetrahedron Lett., 1997, 38, 4957; (b) B. Krzyżanowska, K. He, A. Hasan, B. Ramsay Shaw, Tetrahedron, 1998, 54, 5119; (c) K. He, A. Hasan, B. Krzyżanowska, B. Ramsay Shaw, J. Org. Chem., 1998, 63, 5769; (d) A.P. Higson, A. Sierzchała, H. Brummel, Z. Zhao, M.H. Caruthers, Tetrahedron Lett., 1998, 39, 3899; (e) D.S. Sergueev, B. Ramsay Sha, J. Am. Chem. Soc., 1998, 120, 9417; f) Z.A. Sergueeva, D.S. Sergueev, B. Ramsay Shaw, Tetrahedron Lett., 1999, 40, 2041; (g) K.E. Jenkins, A.P. Higson, P.H. Seeberger, M.H. Caruthers, J. Am. Chem. Soc., 2002, 124, 6584; (h) P. Li, B. Ramsay Shaw, Org. Lett., 2002, 4, 2009.
- [10] (a) J.M. Brunel, B. Faure, M. Maffei, Chem Rev., 1998, 178-180, 665; (b) H. Ohf, J. Holz, M. Quirmbach, A. Börner, Synthesis, 1998, 1391.
- [11] Znane są jedynie dwa przypadki, w których zaobserwowano trwałą trójwiązalną formę kwasu fosfinawego: (a) J.E. Griffiths, A.B. Burg, J. Am. Chem. Soc., 1960, 82, 1507, J.E. Griffiths, A.B. Burg, J. Am. Chem. Soc., 1962, 84, 3442; (b) D.D. Magnelli, G. Tesi, J.U. Lowe, W.E. McQuistion, Inorg Chem., 1966, 5, 457.
- [12] M. Stankevič, K.M. Pietrusiewicz, Synlett, 2003, 1012.
- [13] (a) M.E.D. Hillman, J. Am. Chem. Soc., 1962, 84, 4715; (b) M.E.D. Hillman, J. Am. Chem. Soc., 1963, 85, 982; (c) M.E.D. Hillman, J. Am. Chem. Soc., 1963, 85, 1626.
- [14] S. Oae, Y. Uchida, Acc. Chem. Res., 1991, 24, 202 i prace tam cytowane.
- [15] K. Issleib, B. Walther, Z. Chem., 1968, 8, 67.
- [16] J. Drabowicz, P. Łyżwa, J. Omelańczuk, K.M. Pietrusiewicz, M. Mikołajczyk, Tetrahedron: Asymmetry, 1999, 10, 2757.
- [17] T. Reetz, J. Am. Chem. Soc., 1960, 82, 5039.
- [18] M. Stankevič, G. Andrijewski, K.M. Pietrusiewicz, Synlett, 2004, 313.
- [19] M. Stankevič, K.M. Pietrusiewicz, Synthesis, 2005, 1279
- [20] (a) A.-C. Gaumont, K. Bourumeau, J.-M. Denis, P. Guenot, J. Organomet. Chem., 1994, 484, 9; (b) P. Shapland, E. Vedejs, J. Org. Chem., 2004, 69, 4094.
- [21] M. Stankevič, Praca doktorska, Instytut Chemii Organicznej Polskiej Akademii Nauk, Warszawa, 2004.
- [22] K.M. Pietrusiewicz, M. Stankevič, Curr. Org. Chem., 2005, 9, 1883.
- [23] M. Stankevič, K.M. Pietrusiewicz, w przygotowaniu.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS2-0010-0012