Prolina – pospolity aminokwas wyjątkowy katalizator. Część II, Międzycząsteczkowa kondensacja aldolowa

Kołodziejska, R.; Wróblewski, M.; Karczmarska-Wódzka, A.; Studzińska, R.; Dramiński, M.

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Tytuł artykułu

Prolina – pospolity aminokwas wyjątkowy katalizator. Część II, Międzycząsteczkowa kondensacja aldolowa

Autorzy

Kołodziejska R. , Wróblewski M. , Karczmarska-Wódzka A. , Studzińska R. , Dramiński M.

Treść / Zawartość

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Warianty tytułu

Proline as a common amino acid and an exceptional catalyst. Part II, Intermolecular aldol reaction

Języki publikacji

Abstrakty

Proline in organic synthesis is used as a small molecular organocatalyst. In a catalytic act proline, similarly to an enzyme, activates reagents, stabilizes transition state and influences an orientation of substrates [1–12]. Proline works as aldolase I (so called microaldolase I). In comparison with other amino acids it shows exceptional nucleophilicity which makes imines and enamines formation easier. In the intermolecular aldol reaction proline was used for the first time by List and co-workers (Scheme 1) [3, 9, 20]. Since then an immense progress has been observed in this field. Several aldolization reactions were performed in the presence of proline. Reactions of this type proceed between the donor (nucleophile) and the acceptor (electrophile). In aldol reaction the donors can be both ketones and aldehydes which next are condensed with ketones and aldehydes acting as electrophiles (Scheme 2–18; Tab. 1–7) [21–72]. The presence of proline ensures not only high yield of homo- and heteroaldolization but mainly enables conducting enantio- and diastereoselective synthesis. Intermolecular proline-catalyzed aldol condensation proceeds according to enamine mechanism. Anti-aldols, which make a valuable source of intermediates in the synthesis of important biologically active compounds, are mainly obtained in this reaction [35–44, 54, 58, 62, 63, 68, 69, 71].

Słowa kluczowe

międzycząsteczkowa reakcja aldolowa donor akceptor prolina anti-aldole

intermolecular aldol reaction donor acceptor proline anti-aldol

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2013

Tom

[Z] 67, 11-12

Strony

1027--1050

Opis fizyczny

Bibliogr. 72 poz., schem., tab.

Twórcy

autor

Kołodziejska R.

renatakol@poczta.fm

Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika Collegium Medicum w Bydgoszczy ul. Dębowa 3, 85-626 Bydgoszcz

autor

Wróblewski M.

Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika Collegium Medicum w Bydgoszczy ul. Dębowa 3, 85-626 Bydgoszcz

autor

Karczmarska-Wódzka A.

Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika Collegium Medicum w Bydgoszczy ul. Dębowa 3, 85-626 Bydgoszcz

autor

Studzińska R.

Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika Collegium Medicum w Bydgoszczy ul. Dębowa 3, 85-626 Bydgoszcz

autor

Dramiński M.

Katedra i Zakład Chemii Ogólnej Uniwersytetu Mikołaja Kopernika Collegium Medicum w Bydgoszczy ul. Dębowa 3, 85-626 Bydgoszcz

Bibliografia

[1] S.K. Panday, Tetrahedron: Asymmetry, 2011, 22, 1817.
[2] S.G. Zlotin, A.S. Kucherenko, I.P. Beletskaya, Russian Chemical Reviews, 2009, 78, 737.
[3] B. List, Tetrahedron, 2002, 58, 5573.
[4] B. List, Acc. Chem. Res., 2004, 4, 548.
[5] P.I. Dalko, Enantioselective Organocatalysis: Reactions and Experimental Procedures, Wiley-VCH Verlag GmbH & Co. KgaA Weinheim, 2007.
[6] M.J. Gaunt, C.C.C., Johansson, A. McNally, N.T. Vo, Drug Discovery Today, 2007, 12, 8.
[7] M. Movassaghi, E.N. Jacobsen, Science, 2002, 298, 1904.
[8] M. Stodulski, J. Młynarski, Wiad. Chem., 2010, 64, 5.
[9] H. Groger, J. Wilken, Angew. Chem. Int. Ed., 2001, 40, 529.
[10] C. Palomo, M. Oiarbide, J.M. Garcia, Chem. Eur. J., 2002, 8, 37.
[11] J. Seayad, B. List, Org. Biomol. Chem., 2005, 3, 719.
[12] B. Alcaide, P. Almendros, Eur. J. Org. Chem., 2002, 1595.
[13] S. Bahmanyar, K.N. Houk, H.J. Martin, B. List, J. Am. Chem. Soc., 2003, 125, 2475.
[14] S. Bahmanyar, K.N. Houk, J. Am. Chem. Soc., 2001, 123, 12911.
[15] B. List, L. Hoang, H.J. Martin, PNAS, 2004, 101, 5839.
[16] B. List, Chem. Commun., 2006, 819.
[17] D.A. Bock, Ch.W. Lehmann, B. List, PNAS, 2010, 107, 20636.
[18] W. Notz, F. Tanaka, C.F. Barbas III, Acc. Chem. Res., 2004, 37, 580.
[19] B. List, R.A. Lerner, C.F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395.
[20] B. List, P. Pojarliev, Ch. Castello, Organic Letter, 2001, 4, 573.
[21] K. Sakthivel, W. Notz, T. Bui, C.F.F. Barbas III, J. Am. Chem. Soc., 2001, 123, 5260.
[22] J. Casas, H. Sunden, A. Cordova, Tetrahedron Letters, 2004, 45, 6117.
[23] Q. Pan, B. Zou, Y. Wang, D. Ma, Org. Lett., 2004, 6, 1009.
[24] I. Kumar, C.V. Rode, Tetrahedron: Asymmetry, 2006, 17, 763.
[25] I. Kumar, C.V. Rode, Tetrahedron: Asymmetry, 2007, 18, 1975.
[26] I. Izquierdo, M.T. Plaza, R. Robles, A.J. Mota, F. Franco, Tetrahedron: Asymmetry, 2001, 12, 2749.
[27] K. Funabiki, H. Yamamoto, H. Nagaya, M. Matsui, Tetrahedron Letters, 2006, 47, 5507.
[28] B. Alcaide, P. Almendros, A. Luna, M.R. Torres, J. Org. Chem., 2006, 71, 4818.
[29] D. Enders, T. Gasperi, Chem. Commun., 2007, 88.
[30] A.M. Bernard, A. Frongia, P.P. Piras, F. Secci, M. Spiga, Tetrahedron Letters, 2008, 49, 3037.
[31] W. Notz, B. List, J. Am. Chem. Soc., 2000, 122, 7386.
[32] H. Liu, L. Peng, T. Zhang, Y. Li, New. J. Chem., 2003, 27, 1159.
[33] D. Enders, M. Voith, A. Lenzen, Angew. Chem. Int. Ed., 2005, 44, 1304.
[34] A. Cordova, W. Notz, C.F. Barbas III, J. Org. Chem., 2002, 67, 301.
[35] J.T. Suri, S. Mitsumori, K. Albertshofer, F. Tanaka, C.F. Barbas III, J. Org. Chem., 2006, 71, 3822.
[36] J.T. Suri, D.B. Ramachary, C.F. Barbas III, Org. Lett., 2005, 7, 1384.
[37] Ch. Grondal, D. Enders, Tetrahedron, 2006, 62, 329.
[38] Ch. Grondal, D. Enders, Ad. Synth. Catal., 2007, 349, 694.
[39] D. Enders, Ch. Grondal, Angew. Chem. Int. Ed., 2005, 44, 1210.
[40] I. Ibrahem, W. Zou, Y. Xu, A. Cordova, Adv. Synth. Catal., 2006, 348, 211.
[41] D. Enders, A.A. Narine. Org. Chem., 2008, 73, 7857.
[42] D. Enders, J. Paleček, Ch. Grondal, Chem. Commun., 2006, 655.
[43] F. Calderon, E.G. Doyaguez, A. Fernandez-Mayoralas, J. Org. Chem., 2006, 71, 6258.
[44] F. Calderon, E.G. Doyaguez, P.H.-Y. Cheong, A. Fernandez-Mayoralas, K.N. Houk, J. Org. Chem., 2008, 73, 7916.
[45] J. Mlynarski, B. Gut, Chem. Soc. Rev., 2012, 41,587.
[46] I. Ibrahem, A. Cordova, Tetrahedron Letters, 2005, 46, 3363.
[47] N. Zotova, A. Franzke, A. Armstrong, D.G. Blackmond, J. Am. Chem. Soc., 2007, 129, 15100.
[48] M. Raja, V.K. Singh, Chem. Commun., 2009, 6687.
[49] M. Gruttadauria, F. Giacalone, R. Notoa, Adv. Synth. Catal. 2009, 351, 33.
[50] L.-H. Qiu, , Z.-X. Shen, Ch.-Q. Shi, Y.-H. Liu, Y.-W. Zhang, Chin. J. Chem., 2005, 23, 584.
[51] O. Tokuda, T. Kano, W.-G. Gao, T. Ikemoto, K. Maruoka, Org. Lett., 2005, 7, 5103.
[52] J. Xiang, B. Li, Chin. J. Chem., 2010, 28, 617.
[53] Y. Wang, Z. Shen, B. Li, Y. Zhang, Y. Zhang, Chem. Commun., 2007, 1284.
[54] S. Samanta, C.-G. Zhao, J. Am. Chem. Soc., 2006, 128, 7442.
[55] S. Samanta, S. Perera, C.-G. Zhao, J. Org. Chem., 2010, 75, 1101.
[56] A.B. Northrup, D.W.C. MacMillan, J. Am. Chem. Soc., 2002, 124, 6798.
[57] R. Thayumanavan, F. Tanaka, C.F. Barbas III, Org. Lett., 2004, 6, 3541.
[58] R.I. Storer, D.W.C. Macmillan, Tetrahedron, 2004, 60, 7705.
[59] N. Mase, F. Tanaka, C.F. Barbas III, Angew. Chem. Int. Ed., 2004, 43, 2420.
[60] A. Cordova, W. Notz, C.F. Barbas III, J. Org. Chem., 2002, 67, 301.
[61] N.S. Chowdari, D.B. Ramachary, A. Cordova, C.F. Barbas, III, Tetrahedron Letters, 2002, 43, 9591.
[62] J. Casas, M. Engqvist, I. Ibrahem, B. Kaynak, A. Cordova, Angew. Chem. Int. Ed., 2005, 44, 1343.
[63] U. Kazmaier, Angew. Chem. Int. Ed., 2005, 44, 2186.
[64] G.-L. Zhao, W.-W. Liao, A. Cordova, Tetrahedron Letters, 2006, 47, 4929.
[65] A.B. Northrup, I.K. Mangion, F. Hettche, D.W.C. MacMillan, Angew. Chem. Int. Ed., 2004, 43, 2152.
[66] A. Cordova, M. Engqvist, I. Ibrahem, J. Casas, H. Sunden, E. Chem. Commun, 2005, 2047.
[67] A. Cordova, I. Ibrahem, J. Casas, H. Sunden, M. Engqvist, E. Reyes, Chem. Eur. J., 2005, 11, 4772.
[68] P.M. Pihko, A. Erkkila, Tetrahedron Lett., 2003, 44, 7607.
[69] A.B. Northrup, D.W.C. MacMillan, Science, 2004, 305, 1752.
[70] D. Hazelard, H. Ishikawa, D. Hashizume, H. Koshino, Y. Hayashi, Org. Lett.,2008, 10, 1445.
[71] S. Hajra, A.K. Giri, S. Hazra, J. Org. Chem., 2008, 73, 3935.
[72] A. Bogevig, N. Kumaragurubaran, K.A. Jorgensen, Chem. Commun., 2002, 620.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-e7b1b715-c8e2-40a8-ae04-88eddf34115b