PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Chiralne katalizatory organiczne w asymetrycznej reakcji Michaela

Identyfikatory
Warianty tytułu
EN
Chiral organocatalysts in asymmetric Michael reaction
Języki publikacji
PL
Abstrakty
EN
In marked contrast to enantioselective Michael reactions promoted by chiral Lewis acids, organocatalytic Michael reactions have not been used as standard transformation in organic chemistry until quite recently. During the past few years chiral organocatalysts have emerged as a broadly applicable class of catalysts for enantioselective Michael reaction. This review summarizes these advances emphasizing the structural and mechanistic features that contribute to high enantioselectivity in organocatalytic Michael reactions. The first part of this review deals with the development of covalent catalysis in organocatalytic asymmetric Michael reactions. To date, several chiral secondary amines have been employed to promote formation of electron-rich enamines from enolizable aldehydes and ketones, which then react with various ?,?-unsaturated electrophiles to afford products [7-24]. In contrast, chiral imidazolidinones and diarylprolinol ethers are most often used to activate ?,?-unsaturated carbonyl compounds by forming electron-deficient iminium ions, which render the ?-carbon more electrophilic then their carbonyl precursors for nucleophilic attack [2a, 7, 25-34]. The second part of this review documents the development of non-covalent catalysis [35-64]. In this regard, chiral Bronstedt bases [35-39], chiral phase-transfer catalysts [40-49] and chiral hydrogen-bond donors [50-64] have emerged in the past few years as readily accessible organocatalysts of asymmetric Michael reaction. The most efficient catalysts such as cinchona alkaloids and their derivatives, quaternary ammonium salts obtained from cinchona alkaloids and chiral thiourea derivatives, respectively are revived and the modes of actions are discussed. Furthermore, the major developments of organocatalytic asymmetric Michael reactions are also reviewed.
Rocznik
Strony
391--436
Opis fizyczny
bibliogr. 64 poz., wykr.
Twórcy
autor
autor
  • Instytut Chemii Organicznej, Wydział Chemiczny, Politechnika Łódzka, ul. Żeromskiego 116, 90-924 Łódź, henkrawc@p.lodz.pl
Bibliografia
  • [1] (a) P.L. Dalko, L. Moisan, Angew. Chem. Int. Ed., 2004, 43, 5138. (b) A. Berkessel, H. Gröger, A symmetric Organocatalysis, VCH : Weinheim, Germany, 2004. (c) Acc. Chem. Res., 2004, 37 (8), zeszyt poświęcony organokatalizie. (d) J. Seayed, B. List, Org. Biomol. Chem., 2005, 3, 719. (e) B. List, J.-W. Yang, Science, 2006, 313, 1584. (f) B. List, Chem. Comm., 2006, 819. (g) M.J. Gaunt, C.C.C. Johansson, A. McNally, N.C. Vo, Drug Discovery Today, 2007, 2, 8. (h) P.I. Dalko, Enantioselective Organocatalysis, Wiley-VCH , Weinheim, 2007. (i) Chem. Rev., 2007, 107 (12), zeszyt poświęcony organokatalizie. (j) A. Dondoni, A. Massi, Angew. Chem. Int. E d., 2008, 47, 4638. (j) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. Int. Ed., 2008, 47, 6138.
  • [2] (a) G. Lelais, D.W.C. MacMillan, Aldrichim. Acta, 2006, 39, 79. (b) J.L. Vicario, D. Badía, L . Carrillo, Synthesis, 2007, 2065. (c) D. Almasi, D.A. Alonso, C. Najera, Tetrahedron: Asymmetry, 2007, 18, 299. (d) S.B. Tsogoeva, Eur. J. Org. Chem., 2007, 1701. (e) S. Sulzer-Mossé, A . Alexakis, Chem. Commun., 2007, 3123.
  • [3] K .A. Ahrendt, C.J. Borths, D.W.C. MacMillan, J. Am. Chem. Soc., 2000, 122, 4243.
  • [4] G. Bredig, W.S. Fiske, Biochem., Z. 1912, 7.
  • [5] (a) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed., 1971, 10, 496; (b) Z.G. Hajos, D.R. Parrish, J. Org. Chem., 1974, 39, 1615.
  • [6] (a) B. List, R.A. Lerner, C.F. Barbas III , J. Am. Chem. Soc., 2000, 122, 2395; (b) B. List, Tetrahedron, 2002, 58, 5573.
  • [7] (a) C. Palomo, A. Mielgo, Angew. Chem. Int. Ed., 2006, 45, 7876; (b) A. Mielgo, C. Palomo, Chem. Asian J., 2008, 3, 922; (c) J. Franzén, M. Marigo, D. Fielenbach, T.C. Wabnitz, A . Kjærsgaard, K.A. Jørgensen, J. Am. Chem. Soc., 2005, 127, 18296.
  • [8] (a) M. Marigo, K.A. Jørgensen, Chem. Commun., 2006, 2001. (b) G. Guillena, D.J. Ramón, Tetrahedron: Asymmetry, 2006, 17, 1465.
  • [9] (a) J.M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, C.F. Barbas III , Synthesis, 2004, 1509. (b) D. Enders, A. Seki, Synlett, 2002, 26. (c) B. List, P. Pojarliev, H.J. Martin, Org. Lett., 2001, 3, 2423.
  • [10] A .J.A. Cobb, D.A. Longbottom, D.M. Shaw, S.L. Ley, Chem. Commun., 2004, 1808.
  • [11] C .E.T. Mitchell, A.J.A. Cobb, S.V. Ley, Synlett, 2005, 611.
  • [12] T . Ishii, S. Fujioka, Y. Sekiguchi, H. Kotsuki, J. Am. Chem. Soc., 2004, 126, 9558.
  • [13] S.V. Pansare, K. Pandya, J. Am. Chem. Soc., 2006, 128, 9624.
  • [14] Y . Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. Int. Ed., 2005, 44, 4212.
  • [15] W . Wang, J. Wang, H. Li, Angew. Chem. Int. Ed., 2005, 44, 1369.
  • [16] J.M. Betancort, C.F. Barbas III , Org. Lett., 2001, 3, 3737.
  • [17] N. Mase, R. Thayumanavan, F. Tanaka, C.F. Barbas III , Org. Lett., 2004, 6, 2527.
  • [18] O . Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal., 2004, 346, 1147.
  • [19] P. Melchiorre, K.A. Jørgensen, J. Org. Chem., 2003, 68, 4151.
  • [20] (a) Y. Chi, S.H. Gellman, Org. Lett., 2005, 7, 4253. (b) T.J. Peelen, Y. Chi, S.H. Gellman, J. Am. Chem. Soc., 2005, 127, 11598.
  • [21] S. Mossé, A. Alexakis, Org. Lett., 2005, 7, 4361.
  • [22] G.-L. Zhao, Y. Xu, H. Sundén, L. Eriksson, M. Sayah, A. Córdova, Chem. Commun., 2007, 734.
  • [23] C .-L. Cao, X.-L. Sun, J.-L. Zhou, Y. Tang, J. Org. Chem., 2007, 72, 4073.
  • [24] S. Sulzer-Mossé, M. Tissot, A. Alexakis, Org. Lett., 2007, 9, 3749.
  • [25] S.P. Brown, N.C. Goodwin, D.W.C. MacMillan, J. Am. Chem. Soc., 2003, 125, 1192.
  • [26] (a) M. Marigo, T.C. Wabnitz, D. Fielenbach, K.A. Jørgensen, Angew. Chem. Int. Ed., 2005, 44, 794. (b) S. Brandau, A. Landa, J. Franzén, M. Marigo, K.A. Jørgensen, Angew. Chem. Int. Ed., 2006, 45, 4305.
  • [27] A . Carlone, M. Marigo, C. North, A. Landa, K.A. Jørgensen, Chem. Commun., 2006, 4928.
  • [28] A . Kawara, T. Taguchi, Tetrahedron Lett., 1994, 35, 8805.
  • [29] N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. Int. Ed., 2003, 42, 661.
  • [30] S. Hanessian, V. Pham, Org. Lett., 2000, 2, 2975.
  • [31] S. Hanessian, Z. Shao, J. S. Warrier, Org. Lett., 2006, 8, 4787.
  • [32] L . Hojabri, A. Hartikka, F.M. Moghaddam, P.I. Arvidsson, Adv. Synth. Catal., 2007, 349, 740.
  • [33] (a) S.B. Tsogoeva, S.B. Jagtap, Z.A. Ardemasova, Tetrahedron: Asymmetry, 2006, 17, 989. (b) S.B. Tsogoeva, S.B. Jagtap, Z.A. Ardemasova, V.N. Kalikhevich, Eur. J. Org. Chem., 2004, 4014.
  • [34] (a) N. Halland, R.G. Hazell, K.A. Jørgensen, J. Org. Chem., 2002, 67, 8331. (b) A. Prieto, N. Halland, K.A. Jørgensen, Org. Lett., 2005, 7, 3897.
  • [35] (a) T. Marcelli, J.H. van Maarseveen, H. Hiemstra, Angew. Chem. Int. Ed., 2006, 45, 7496. (b) C.O. Dalaigh, Synlett, 2005, 875. (c) H. Hoffmann, R. Martin, J. Frackenpohl, Eur. J. Org. Chem., 2004, 4293. (d) S.-K. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. R es., 2004, 37, 621. (e) T.P. Yoon, E.N. Jacobsen, Science, 2003, 299, 1691. (f) K. Kacprzak, J. Gawroński, Synthesis, 2001, 961.
  • [36] (a) H. Wynberg, R. Helder, Tetrahedron Lett., 1975, 4057. (b) K. Hermann, H. Wynberg, J. Org. Chem., 1979, 44, 2238. (c) H. Hiemstra, H. Wynberg, J. Am. Chem. Soc., 1981, 103, 417.
  • [37] H . Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc., 2004, 126, 9906.
  • [38] F. Wu, R. Hong, J. Khan, X. Liu, L. Deng, Angew. Chem. Int. Ed., 2006, 45, 4301.
  • [39] (a) D. Xue, Y.-C. Chen, Q.-W. Wang, L.-F. Cun, J. Zhu, J.-G. Deng, Org. Lett., 2005, 7, 5293. (b) T.B. Poulsen, M. Bell, K.A. Jørgensen, Org. Biomol. Chem., 2006, 4, 63. (c) M. Bell, K .A. Jørgensen, J. Am. Chem. Soc., 2004, 126, 5672.
  • [40] (a) T. Ooi, K. Maruoka, Angew. Chem. Int. Ed., 2007, 46, 4222. (b) K. Maruoka, T. Ooi, T. Kano, Chem. Commun., 2007, 1487. (c) B. Lygo, B. I. Andrews, Acc. Chem. Res. 2004, 37, 518. (d) K. Maruoka, T. Ooi, Chem. Rev., 2003, 103, 3013. (e) C. Nájera, Synlett, 2002, 1388.
  • [41] (a) F.-Y. Zhang, E. J. Corey, Org. Lett., 2000, 2, 1097. (b) E. J. Corey, F-Y. Zhang, Org. Lett., 2000, 2, 4257.
  • [42] F.-Y. Zhang, E.J. Corey, Org. Lett., 2001, 3, 639.
  • [43] T . B. Poulsen, L. Bernardi, M. Bell, K.A. Jørgensen, Angew. Chem. Int. Ed., 2006, 45, 6551.
  • [44] T . Tozawa, H. Nagao, Y. Yamane, T. Mukaiyama, Chem. Asian J., 2007, 2, 123.
  • [45] T . Ooi, S. Fujioka, K. Maruoka, J. Am. Chem. Soc., 2004, 126, 11790.
  • [46] T . Ooi, S. Takada, S. Fujioka, K. Maruoka, Org. Lett., 2005, 7, 5143.
  • [47] T . Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc., 2003, 125, 9022.
  • [48] T . Ooi, K. Doda, S. Takada, K. Maruoka, Tetrahedron Lett., 2006, 47, 145.
  • [49] T . Ooi, S. Takada, K. Doda, K. Maruoka, Angew. Chem. Int. Ed., 2006, 45, 7606.
  • [50] (a) T. Akiyama, J. Itoh, J. Fuchibe, Adv. Synth. Catal., 2006, 348, 999. (b) P. Pihko, Angew. Chem. Int. Ed., 2004, 43, 2062. (c) P.N. Schreiner, Chem. Soc. Rev., 2003, 32, 289. (d) M.S. Taylor, E .N. Jacobsen, Angew. Chem. Int. Ed., 2006, 45, 1520. (e) S.J. Connon, Chem. Eur. J., 2006, 12, 5418. (f) Y. Takemoto, Org. Biomol. Chem., 2005, 3, 4299.
  • [51] T . Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc., 2005, 127, 119.
  • [52] S.B. Tsogoeva, D.A. Yalalov, M.J. Hateley, C. Weckbecker, K. Hutchamacher, Eur. J. Org. Chem., 2005, 4995.
  • [53] K . Liu, H.-F. Cui, J. Nie, K.-Y. Dong, X.-J. Li, J.-A. Ma, Org. Lett., 2007, 9, 923.
  • [54] C .-L. Cao, M.-C. Ye, X-L. Sun, Y. Tang, Org. Lett., 2006, 8, 2901.
  • [55] H .-B. Huang, E.N. Jacobsen, J. Am. Chem. Soc., 2006, 128, 7170.
  • [56] Y .-J. Cao, H.-H. Lu, Y.-Y. Lai, L.-Q. Lu, W.-J. Xiao, Synthesis, 2006, 3795.
  • [57] (a) S.B. Tsogoeva, S.-W. Wei, Chem. Commun., 2006, 1451. (b) D.A. Yalalov, S.B. Tsogoeva, S. Schmatz, Adv. Synth. Catal., 2006, 348, 826.
  • [58] (a) T. Inokuma, Y. Hoashi, T. Takemoto Inokuma, Y. Hoashi, K. Takemoto, J. Am. Chem. Soc., 2006, 128, 9423. (b) Y. Hoashi, T. Okino, Y. Takemoto, Angew. Chem. Int. Ed., 2005, 44, 4032.
  • [59] T .-Y. Liu, R. Li, Q. Chai, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Chem. Eur. J., 2007, 13, 319.
  • [60] S.J. Connon, Chem. Commun., 2008, 2499.
  • [61] (a) J. Ye, D.J. Dixon, P.S. Hynes, Chem. Commun., 2005, 4481. (b) P.S. Hynes, D. Stranges, P. A. Stupple, A. Guarna, D.J. Dixon, Org. Lett., 2007, 9, 2107.
  • [62] S.H. McCooey, S.J. Connon, Angew. Chem. Int. Ed., 2005, 44, 6367.
  • [63] S.J. Vakulya, S. Varga, A. Csámpai, T. Soos, Org. Lett., 2005, 7, 1967.
  • [64] B . Wang, F. Wu, Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc., 2007, 129, 768.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS5-0017-0052
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.