PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

2,2’-dihydroksy-1,1’-binaftyl (BINOL) i jego pochodne. Wybrane syntezy i zastosowanie. Część. II

Autorzy
Treść / Zawartość
Identyfikatory
Warianty tytułu
EN
2,2’-dihydroxy-1,1’-binaphthyl (BINOL) and its derivatives : selected synthesis methods and applications. Part II
Języki publikacji
PL
Abstrakty
EN
An invention of new catalytic strategies for stereoselective synthesis is of current interest to many laboratories worldwide . Over the past few decades a remark - able progress in the field of stereocontrolled synthesis has been achieved with chiral 1,1’-binaphthyl compounds. Optically active 1,1’-binaphthyl-2,2’-diol (BINOL) and its derivatives due to their axial dissymmetry and molecular flexibility have been widely utilized as chiral ligands and auxiliaries in stoichiometric or catalytic asymmetric reactions, such as metal-catalysed transformations and enantioselective organocatalysis. BINOL and its functionalized analogues have demonstrated remark - able chiral discrimination properties. Extensive studies on molecular recognition provided the successful results in the application of BINOL as a host for an optical resolution of racemic guests and as a chiral NMR shift reagent for the determination of chiral compounds. It has been found that the axial chirality of binaphthyl units in host molecules is crucial contribution to their stereoselctive complexation with chiral guests.
Rocznik
Strony
55--92
Opis fizyczny
Bibliogr. 72 poz., schem., tab.
Twórcy
autor
  • Centrum Badań Molekularnych i Makromolekularnych w Łodzi, Polska Akademia Nauk ul. Sienkiewicza 112, 90-363 Łódź, Poland
Bibliografia
  • [1] R. Noyori, 1. Tomino, Y. Tanimoto, J. Am. Chem. Soc., 1979, 101, 3129.
  • [2] R. Noyori, I. Tomino, Y. Tanimoto, M. Nishizawa, J. Am. Chem. Soc., 1984, 106, 6709.
  • [3] A. Ford, S. Woodward, Angew. Chem. Int. Ed., 1999, 38, 335.
  • [4] Y. Xu, G.C. Clarkson, G. Docherty, C. L. North, G. Woodward, M. Wills, J. Org. Chem. 2005, 70, 8079.
  • [5] C.S. Weinert, P.E. Fanwick, I.P. Rothwell, Organometallics, 2005, 24, 5759.
  • [6] Y. Xiao, S.V. Malhotra, Tetrahedron: Asymmetry, 2006, 17, 1062.
  • [7] C.R. Graves, H. Zhou, C.L. Stern, S.T. Nguyen, J. Org. Chem., 2007, 72, 9121.
  • [8] M. Lorca, D. Kuhn, M. Kurosu, Tetrahedron Lett., 2001, 42, 6243.
  • [9] R.O. Hutchins, A. Abdel-Magid, Y.P. Stercho, A. Wambsgans, J. Org. Chem., 1987, 52, 702.
  • [10] T. Kawate, M. Nakagawa, T. Kakikawa, T. Hino, Tetrahedron: Asymmetry 1992, 3, 227.
  • [11] M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett., 2005, 7, 3781.
  • [12] S. Hoffmann, A.M. Seayad, B. List, Angew. Chem., Int. Ed., 2005, 44, 7424.
  • [13] G. Li, Y. Liang, J.C. Antilla, J. Am. Chem. Soc., 2007, 129, 5830.
  • [14] Q. Kang, Z.-A. Zhao, S.-L. You, Adv. Synth. Catal., 2007, 349, 1657; Corrigendum: Adv. Synth. Catal., 2007, 349, 2075.
  • [15] T.B. Nguyen, H. Bosserouel, Q. Wang, F. Gueritte, Org. Lett., 2010, 12, 4705.
  • [16] C. Zhu, T. Akiyama, Org. Lett., 2009, 11, 4180.
  • [17] C. Zhu, T. Akiyama, Adv. Synth. Catal., 2010, 352, 1846.
  • [18] A. Henseler, M. Kato, K. Mori, T. Akiyama, Angew. Chem. Int. Ed., 2011, 50, 8180.
  • [19] M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc., 1997, 119, 2329.
  • [20] T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 2725.
  • [21] T. Ohshima, V. Gnanadesikan, T. Shibuguchi, Y. Fukuta, T. Nemoto, M. Shibasaki, J. Am. Chem. Soc., 2003, 125, 11206.
  • [22] T. Ohshima, T. Nemoto, S.-y. Tosaki, H. Kakei, V. Gnanadesikan, M. Shibasaki, Tetrahedron 2003, 59, 10485.
  • [23] T. Nemoto, H. Kakei, V. Gnanadesikan, S. Tosaki, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 2002, 124, 14544.
  • [24] T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 9474.
  • [25] R. Kino, K. Daikai, T. Kawanami, H. Furuno, J. Inanaga, Org. Biomol. Chem., 2004, 2, 1822.
  • [26] A. Minatti, K.H. Dotz, Synlett, 2004, 9, 1634.
  • [27] A. Minatti, K.H. Dotz, Eur. J. Org. Chem., 2006, 268.
  • [28] P. Pitchen, H.B. Kagan, Tetrahedron Lett., 1984, 25, 1049.
  • [29] P. Pitchen, E. Dunach, M.N. Deshmukh, H.B. Kagan, J. Am. Chem. Soc., 1984, 106, 8188.
  • [30] F. Di Furia, G. Modena, R. Seraglia, Synthesis, 1984, 325.
  • [31] T. Katsuki, K.B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974.
  • [32] G.E. O’Mahony, P. Kelly, S.E. Lawrence, A.R. Maguire, Arkivoc, 2011, 1, 1.
  • [33] N. Kamatsu, Y. Nishibayashi, T. Sugita, S. Uemura, Tetrahedron Lett., 1992, 33, 5391.
  • [34] N. Kamatsu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem., 1993, 58, 4529.
  • [35] C. Bolm, O.A.G. Dabard, Synlett, 1999, 360.
  • [36] G.D. Sala, A. Lattanzi, T. Severino, A. Scettri, J. Mol. Catal. A: Chem., 2001, 170, 219.
  • [37] L.J.P. Martyn, S. Pandiaraju, A.K. Yudin, J. Organomet. Chem., 2000, 603, 98.
  • [38] X-y. Yuan, X-t. Wang, J. Chongqing Univ. (Engl. Ed.) 2008, 7, 179.
  • [39] Y.-C. Jeong, S. Choi, Y.D. Hwang, K.-H. Ahn, Tetrahedron Lett., 2004, 45, 9249.
  • [40] Y.-C. Jeong, Y.D. Huang, S. Choi, K.-H. Ahn, Tetrahedron: Asymmetry, 2005, 16, 3497.
  • [41] H. Egami, T. Katsuki, J. Am. Chem. Soc., 2007, 129, 8940.
  • [42] C. Kokubo, T. Katsuki, Tetrahedron 1996, 52, 13895.
  • [43] T. Miyazaki, T. Katsuki, Synlett, 2003, 1046.
  • [44] K. Matsumoto, T. Yamaguchi, J. Fujisaki, B. Saito, T. Katsuki, Chem.-Asian J., 2008, 3, 351.
  • [45] M.A.M. Capozzi, C. Cardellicchio, G. Fracchiolla, F. Naso, P. Tortorella, J. Am. Chem. Soc., 1999, 121, 4708.
  • [46] N. Komatsu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem., 1993, 58, 7624.
  • [47] X. Jia, X. Li, L. Xu, Y. Li, Q. Shi, T.T.L. Au-Yeung, C.W. Yip, X. Yao, A.S.C. Chan, Adv. Synth. Catal., 2004, 346, 723.
  • [48] T.R. Kelly, A. Whiting, N.S. Chandrakumar, J. Am. Chem. Soc., 1986, 108, 3510.
  • [49] K. Maruoka, A.B. Concepcion, H. Yamamoto, Bull. Chem. Soc. Jpn., 1992, 65, 3501.
  • [50] M.T. Reetz, S.H. Kyung, C. Bolm, T. Zierke, Chem. Ind., 1986, 824.
  • [51] Y. Motoyama, M. Terada, K. Mikami, Synlett, 1995, 9, 967.
  • [52] D. Kaufmann, R. Boese, Angew. Chem. Int. Ed. Engl., 1990, 29, 545.
  • [53] T.J. Wenzel, Discrimination of chiral compounds using NMR spectroscopy, Ed.: John Wiley & Sons, New Yersey, 2007, 144.
  • [54] F. Toda, K. Mori, J. Okada, M. Node, A. Itoh, Chem. Lett., 1988, 10, 37.
  • [55] F. Toda, K. Mori, A. Sato, Bull. Chem. Soc. Jpn., 1988, 61, 4167.
  • [56] J. Drabowicz, H. Duddeck, Sulfur Chem., 1989, 10, 37.
  • [57] D.P. Reynolds, J.C. Hollerton, S.A. Richards, Analytical Applications of Spectroscopy, C.S. Creaser, A.M.C. Davies, Ed.: Royal Society of Chemistry, London, 1988, 346.
  • [58] B.A. Dawson, D.B. Black, A. Lavoie, M.J. LeBelle, J. Forensic Sci. Int., 1994, 39, 1026.
  • [59] M.J. LeBelle, C. Savard, B.A. Dawson, D.B. Black, L.K. Katyal, F. Zrcek, A.W. By, J. Forensic Sci. Int.,1995, 71, 215.
  • [60] A. Iuliano, D. Bartalucci, G. Uccello-Barretta, F. Balzano, P. Salvadori, Eur. J. Org. Chem., 2001, 2177.
  • [61] J. Reeder, P.P. Castro, C.B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem., 1994, 59, 3151.
  • [62] M. Michalik, C. Dobler, Tetrahedron, 1990, 46, 7739.
  • [63] C. Koy, M. Michalik, C. Dobler, G. Oehme, J. Prakt. Chem., 1997, 339, 660.
  • [64] M. Ardej-Jakubisiak, R. Kawęcki, Tetrahedron: Asymmetry, 2008, 19, 2645.
  • [65] F. Toda, K. Tanaka, S. Nagamatsu, Tetrahedron Lett., 1984, 25, 4929.
  • [66] F. Toda, K. Tanaka, T.C.W. Mak, Chem. Lett., 1984, 2085.
  • [67] J. Drabowicz, J.C. Martin, Tetrahedron: Asymmetry, 1993, 4, 297.
  • [68] J. Drabowicz, P. Łyżwa, J. Omelańczuk, K.M. Pietrusiewicz. M. Mikołajczyk, Tetrahedron: Asymmetry, 1999, 10, 2757.
  • [69] J. Drabowicz, A. Łopusiński, D. Krasowska, zgłoszenie patentowe.
  • [70] K.M. Kim, W.W. Nam, H.J. Park, J. Chin, US7268252B2, 11.09.2007.
  • [71] J. Bunzen, U. Kiehne, C. Benkhauser-Schunk, A. Lutzen, Org. Lett., 2009, 11, 4786.
  • [72] J. Deng, J. Zhu, J. Liao, J. Zhu, PCT/CN2009/071304, 21.10.2010.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-0eb57f79-ae63-4d72-8b7e-d0cbf52b1536
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.