Trans-1,2-diaminocykloheksan – niezwykła kariera outsidera

Petryk, M.; Kwit, M.

Artykuł - szczegóły

Tytuł artykułu

Trans-1,2-diaminocykloheksan – niezwykła kariera outsidera

Autorzy

Petryk M. , Kwit M.

Treść / Zawartość

Pełne teksty:

Pobierz

Identyfikatory

Warianty tytułu

Trans-1,2-diaminocyclohexane – unprecedented outsider’s career

Języki publikacji

Abstrakty

An enantiopure trans-1,2-diaminocyclohexane is one of the most widely used chiral diamines in modern organic chemistry. This chiral building block, readily available from waste industrial products, emerges as a major figure in the field of asymmetric synthesis. The unique structural and conformational properties of trans-1,2-diaminocyclohexane make it very useful for the development of new synthetic strategies, taking advantage of its geometrical pre-organization. In this short article, we will highlight the utility of enantiomerically pure trans-1,2-diaminocyclohexane derivatives as broad-range chiral reagents and ligands for catalytic cycles. A brief overview of the aspects of applications in the field of molecular recognition will also be given.

Słowa kluczowe

struktura chiralność konformacja synteza asymetryczna rozpoznanie molekularne

structure chirality conformation asymmetric synthesis molecular recognition

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2013

Tom

[Z] 67, 5-6

Strony

393--442

Opis fizyczny

Bibliogr. 192 poz., rys., schem.

Twórcy

autor

Petryk M.

Zakład Stereochemii Organicznej Wydział Chemii Uniwersytetu im. Adama Mickiewicza ul. Grunwaldzka 6, 60-780 Poznań

autor

Kwit M.

Marcin.Kwit@amu.edu.pl

Zakład Stereochemii Organicznej Wydział Chemii Uniwersytetu im. Adama Mickiewicza ul. Grunwaldzka 6, 60-780 Poznań

Bibliografia

[1] G. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schaumann, Stereoselective Synthesis, Georg Thieme Verlag, Stuttgard-New York 1996.
[2] K. Kacprzak, J. Gawroński, Synthesis, 2001, 961.
[3] Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, Ch.E. Songa (ed.), Wiley-VCh, Weinheim 2009.
[4] H.C. Kolb, M.S. van Nieuwenhze, K.B. Sharpless, Chem. Rev., 1994, 94, 2487.
[5] T.P. Yoon, E.N. Jacobsen, Science, 2003, 299, 1691.
[6] J. Gawroński, K. Gawrońska, Tartaric and Malic Acids in Synthesis – A Source Book of Building Blocks, Ligands, Auxiliaries, and Resolving Agents, Wiley, New York 1999.
[7] D. Seebach, A.K. Beck, A. Heckel, Angew. Chem., Int. Ed., 2001, 40, 92.
[8] Y.L. Bennani, S. Hanessian, Chem. Rev., 1997, 97, 3161.
[9] J.L. Misset, H. Bleiberg, W. Sutherland, M. Bekradda, E. Cvitkovic, Crit. Rev. Oncol.: Hematol., 2000, 35, 75.
[10] H. Wieland, O. Schlichting, W. von Langsdorff, Z. Phys. Chem., 1926, 161, 74.
[11] M. Chandrasekhar, G. Sekar, V.K. Singht, Tetrahedron Lett., 2000, 41, 10079.
[12] I.A. O’Neil, E. Cleator, J.M. Southern, J.F. Bickley, D.J. Topolczay, Tetrahedron Lett., 2001, 42, 8251.
[13] F. Galsbol, P. Steenbol, B.S. Sorensen, Acta. Chem. Scand., 1972, 26, 3605.
[14] T.A. Whitney, J. Org. Chem., 1980, 45, 4214.
[15] U. Rychlewska, J. Mol. Struct., 1999, 474, 235.
[16] A. Galland, V. Dupray, A. Lafontaine, B. Berton, M. Sanselme, H. Atmani, G. Coquerel, Tetrahedron: Asymmetry, 2010, 21, 2212.
[17] I. Alfonso, C. Astorga, F. Rebolledo, V. Gotor, Chem. Commun., 1996, 2471.
[18] I. Alfonso, Curr. Org. Synth., 2010, 7, 1.
[19] R. Barbucci, P. Paoletti, A. Vacca, J. Chem. Soc. (A), 1970, 2202.
[20] H. Friebolin, Basic One- and Two Dimensional NMR Spectroscopy, VCH 1993.
[21] Comprehensive Chiroptical Spectroscopy, N. Berova, R. Woody, K. Nakanishi, P. Polavarapu (eds), Wiley, 2012.
[22] M. Kwit, Wiad. Chem., 2011, 65, 33.
[23] L.J. Ferrugia, R.J. Cross, H.R.L. Barley, Acta. Cryst. E, 2001, 57, 992.
[24] M. Kwit, J. Gawroński, Tetrahedron, 2003, 59, 9323.
[25] Q. Ye, T. Akutagawa, T. Endo, S. Noro, T. Nakamura, R.-G. Xiong, Inorg. Chem., 2010, 49, 8591.
[26] M.T. Reetz, E. Bohres, R. Goddard, Chem. Commun., 1998, 935.
[27] A.-K. Duhme-Klair, G. Vollmer, C. Mars, R. Frohlich, Angew. Chem., Int. Ed., 2000, 39, 1626.
[28] A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry, 2001, 12, 1171.
[29] M. Atoh, H.O. Sorensen, P. Andersen, Acta. Chem. Scand., 1997, 51, 1169.
[30] G.D. Whitener, J.R. Hagadorn, J. Arnold, J. Chem. Soc., Dalton. Trans., 1999, 1249.
[31] A.S. de Sousa, R.D. Hancock, J.H. Reibenspies, J. Chem. Soc., Dalton. Trans., 1997, 2831.
[32] V.A. Jones, S. Sriprang, M. Thornton-Pett, T.P. Kee, J. Organometal. Chem., 1998, 567, 199.
[33] F. Mavellec, S. Collet, D. Deniaud, A. Reliquet, J.-C. Meslin, J. Chem. Soc., Perkin. Trans. 1, 2001, 3128.
[34] H.W. Gorlitzer, M. Spiegler, R. Anwander, Eur. J. Inorg. Chem., 1998, 1009.
[35] B.M. Trost, D.L. van Vranken, Angew. Chem., Int. Ed., 1992, 31, 228.
[36] M.-K. Jeon, K. Kim, J. Chem. Soc., Perkin. Trans. 1, 2000, 3107.
[37] E.H. Charles, L.M.L. Chia, J. Rothery, E.L. Watson, E.J.L. McInnes, R.D. Farley, A.J. Bridgeman, F.E. Mabbs, C.C. Rowlands, M.A. Halcrow, J. Chem. Soc., Dalton. Trans., 1999, 2087.
[38] N.A.H. Male, M. Thornton-Pett, M. Bochmann, J. Chem. Soc., Dalton. Trans., 1997, 2487.
[39] L. Neuville, J. Chastanet, J. Zhu, Tetrahedron Lett., 1999, 40, 7087.
[40] C. Gennari, S. Ceccarelli, U. Piarulli, C.A.G.N. Montalbetti, R.F.W. Jackson, J. Org. Chem., 1998, 63, 5312.
[41] D.A. Conlon, N. Yasuda, Adv. Synth. Catal., 2001, 343, 137.
[42] A. de la Cruz, K.J. Koeller, N.P. Rath, C.D. Spilling, I.C.F. Vasconcelos, Tetrahedron, 1998, 54, 10513.
[43] J.D.G. Correia, A. Domingos, I. Santos, Eur. J. Inorg. Chem., 2000, 1523.
[44] J.F. Remenar, B.L. Lucht, D.B. Collum, J. Am. Chem. Soc., 1997, 119, 5567.
[45] W.-H. Leung, E.Y.Y. Chan, E.K.F. Chow, I.D. Williams, S.-M. Peng, J. Chem. Soc., Dalton. Trans., 1996, 1229.
[46] A. Haikarainen, J. Sipila, P. Pietikainen, A. Pajunen, I. Mutikainen, , J. Chem. Soc., Dalton. Trans., 2001, 991.
[47] J. Balsells, L. Mejorando, M. Phillips, F. Ortega, G. Aguirre, R. Somanathan, P.J. Walsh, Tetrahedron: Asymmetry, 1998, 9, 4135.
[48] K. Ng, R. Somanathan, P.J. Walsh, Tetrahedron: Asymmetry, 2001, 12, 1719.
[49] G. Mlostoń, D. Rygielska, M. Jasiński, H. Heimgartner, Tetrahedron: Asymmetry, 2011, 22, 669.
[50] D. Xu, K. Prasad, O. Repic, T.J. Blacklock, Tetrahedron Lett., 1995, 36, 7357.
[51] M. Kaik, J. Gawroński, Tetrahedron: Asymmetry, 2003, 14, 1559.
[52] Comprehensive Supramolecular Chemistry, tom I, G.W. Gokel (ed.), Pergamon, Oxford 1996.
[53] A. Furstner, Topics in Catalysis, 1997, 4, 285.
[54] A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012.
[55] T.M. Trnka, R.H. Grubbs, Acc. Chem. Res., 2001, 34, 18.
[56] A.V. Chuchuryukin, H.P. Dijkstra, B.M.J.M. Suijkerbuijk, R.J.M. Klein Gebbink, G.P.M. van Klink, A.M. Mills, A.L. Spek, G. van Koten, Angew. Chem., Int. Ed., 2003, 42, 228.
[57] W. Radecka-Paryzek, V. Patroniak, J. Lisowski, Coord. Chem. Rev., 2005, 249, 2156.
[58] L. Pu, Chem. Rev., 1998, 98, 2405.
[59] N.E. Borisova, M.D. Reshetova, Y.A. Ustynyuk, Chem. Rev., 2007, 107, 46.
[60] D. Savoia, A. Gualandi, Curr. Org. Synth., 2009, 6, 102.
[61] D. Savoia, A. Gualandi, Curr. Org. Synth., 2009, 6, 119.
[62] J. Jaźwinski, J.-M. Lehn, R. Meric, J.-P. Vigneron, M. Cesario, J. Guilham, C. Pascard, Tetrahedron Lett., 1987, 28, 3489.
[63] R. Menif, A.E. Martell, Chem. Commun., 1989, 1521.
[64] H. Stetter, J. Marx, Liebigs Ann. Chem., 1957, 605, 59.
[65] K. Gunst, S. Seggewies, E. Breitmaier, Synthesis, 2001, 1856.
[66] H. Houjou, S.-K. Lee, Y. Hishikawa, Y. Nagawa, K. Hiratani, Chem. Commun., 2000, 2197.
[67] H. Zhao, W. Hua, J. Org. Chem., 2000, 65, 2933.
[68] M. Kreysel, F. Vogtle, Synthesis, 1992, 733.
[69] T. Tsubomura, K. Yasaku, T. Sato, M. Morita, Inorg. Chem., 1992, 31, 447.
[70] J. Lisowski, Magn. Reson. Chem., 1999, 37, 287.
[71] J. Lisowski, Inorg. Chem., 2011, 50, 5567.
[72] A. Gonzalez-Alvarez, I. Alfonso, V. Gotor, Chem. Commun., 2006, 2224.
[73] J. Gregoliński, J. Lisowski, T. Lis, Org. Biomol. Chem., 2005, 3, 3161.
[74] A. Alexander, Chem. Rev., 1995, 95, 273.
[75] J. Gao, J.H. Reibenspies, A.E. Martell, Angew. Chem., Int. Ed., 2003, 42, 6008.
[76] J. Gawroński, H. Kołbon, M. Kwit, A. Katrusiak, J. Org. Chem., 2000, 65, 5768.
[77] M. Chadim, M. Budešĭňskŷ, J. Hodačova, J. Zavada, P.C. Junk, Tetrahedron: Asymmetry, 2001, 12, 127.
[78] J. Gawroński, K. Gawrońska, J. Grajewski, M. Kwit, A. Plutecka, U. Rychlewska, Chem. Eur. J., 2006, 12, 1807.
[79] H.F. Nour, A.M. Lopez-Periago, N. Kuhnert, Rapid Commun. Mass Spectrom., 2012, 26, 1070.
[80] J. Gawroński, M. Brzostowska, M. Kwit, A. Plutecka, U. Rychlewska, J. Org. Chem., 2005, 70, 10147.
[81] J. Gawroński, M. Kwit, J. Grajewski, J. Gajewy, A. Długokińska, Tetrahedron: Asymmetry, 2007, 18, 2632.
[82] Z. Li, C. Jablonski, Chem. Commun., 1999, 1531.
[83] S.R. Korupoju, P.S. Zacharias, Chem. Commun., 1998, 1267.
[84] S.R. Korupoju, N. Mangayarkarasi, S. Ameerunisha, E.J. Valente, P.S. Zacharias, J. Chem. Soc., Dalton Trans., 2000, 2845.
[85] M. Kwit, J. Gawroński, Tetrahedron: Asymmetry, 2003, 14, 1303.
[86] M. Paluch, J. Lisowski, T. Lis, Dalton Trans., 2006, 381.
[87] M. Kwit, A. Plutecka, U. Rychlewska, J. Gawroński, A.F. Khlebnikov, S.I. Kozhushkov, K. Rauch, A. de Meijere, Chem. Eur. J., 2007, 13, 8688.
[88] N. Kuhnert, G.M. Rossignolo, A Lopez-Periago, Org. Biomol. Chem., 2003, 1, 1157.
[89] M. Kaik, J. Gawroński, Org. Lett., 2006, 8, 2921.
[90] P. Skowronek, J. Gawroński, Org. Lett., 2008, 10, 4755.
[91] D. Xu, R. Warmuth, J. Am. Chem. Soc., 2008, 130, 7520.
[92] F. Fache, E. Schulz, M.L. Tommasino, M. Lemaire, Chem. Rev., 2000, 100, 2159.
[93] G. Buono, O. Chiodi, M. Wills, Synlett, 1999, 4, 377.
[94] L. Canali, D.C. Sherrington, Chem. Soc. Rev., 1999, 28, 85.
[95] M. Bandini, P.G. Cozzi, A. Umani-Ronchi, Chem. Commun., 2002, 919.
[96] B.M. Trost, D.L. van Vranken, Chem. Rev., 1996, 96, 257.
[97] E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker, L. Deng, J. Am. Chem. Soc., 1991, 113, 7063.
[98] J. Gajewy, M. Kwit, J. Gawroński, Adv. Synth. Catal., 2009, 351, 1055.
[99] S.J. Connon, Chem. Eur. J., 2006, 12, 5418.
[100] E.N. Jacobsen, Acc. Chem. Res., 2000, 33, 421.
[101] P.G. Cozzi, Chem. Soc. Rev. 2004, 33, 410.
[102] T. Katsuki, Chem. Soc. Rev. 2004, 33, 437.
[103] T. Katsuki, [w:] Catalytic Asymmetric Synthesis, I. Ojima (ed.), Willey-VCH, New York 2000, rozdz. 6B
[104] E.N. Jacobsen, M.H. Wu, [w:] Comprehensive Asymmetric Catalysis, E.N. Jacobsen, A. Pfaltz, H. Yamamoto (eds.) Springer-Verlag, Berlin 2000.
[105] E.N. Jacobsen, [w:] Comprehensive Organometallic Chemistry, G. Wilkinson, F.G.A. Stone, E.W. Abel, L.S. Hegedus (eds.) Pergamon Press, New York 1995, rozdz. 11.
[106] T. Katsuki, J. Mol. Cat. A: Chemical, 1996, 113, 87.
[107] T. Katsuki, Adv. Synth. Catal., 2002, 344, 131.
[108] K. Bernardo, S. Leppard, A. Robert, G. Commenges, F. Dahan, B. Meunier, Inorg. Chem., 1996, 35, 387.
[109] H. Sellner, J.K. Karjalainen, D. Seebach, Chem. Eur. J., 2001, 7, 2873.
[110] A. Linker, Angew. Chem., Int. Ed., 1997, 36, 2060.
[111] M. Palucki, N.S. Finney, P.J. Pospisil, M.L. Guler, T. Ishida, E.N. Jacobsen, J. Am. Chem. Soc., 1998, 120, 948.
[112] A. Wlodawer, J. Vondrasek, Annu. Rev. Biophys. Biomol. Struct., 1998, 27, 249.
[113] A. Brik, C.-H. Wong, Org. Biomol. Chem., 2003, 1, 5.
[114] A.K. Ghosh, S. Fidanze, C.H. Senanayake, Synthesis, 1998, 937.
[115] C.H. Senanayake, Aldrichimica Acta, 1998, 31, 3.
[116] US Patent 5,420,353 (Merck, 1995);
[117] US Patent 5,677,469 (Sepracor, 1997).
[118] J. Gawroński, K. Gawrońska, K. Kacprzak, M. Kwit, Wspołczesna synteza organiczna. Wybór eksperymentow, Wydawnictwo Naukowe PWN, Warszawa 2004.
[119] L.E. Martinez, J.L. Leighton, D.H. Carsten, E.N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5897.
[120] J.M. Keith, J.F. Larrow, E.N. Jacobsen, Adv. Synth. Catal., 2001, 343, 5.
[121] B.D. Brandes, E.N. Jacobsen, Synlett, 2001, 1013.
[122] M. Tokunaga, J.F. Larrow, F. Kakiuchi, E.N. Jacobsen, Science, 1997, 277, 936.
[123] S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunaga, K.B. Hansen, A.E. Gould, M.E. Furrow, E.N. Jacobsen, J. Am. Chem. Soc., 2002, 124, 1307.
[124] J.M. Ready, E.N. Jacobsen, J. Am. Chem. Soc., 1999, 121, 6086.
[125] T.S. Reger, K.D. Janda, J. Am. Chem. Soc., 2000, 122, 6929.
[126] E.N. Jacobsen, Acc. Chem. Res., 2000, 33, 421.
[127] J. Salaun, Chem. Rev., 1989, 89, 1247.
[128] M.P. Doyle, D.C. Forbes, Chem. Rev., 1998, 98, 911.
[129] M.P. Doyle, [w:] Catalytic Asymmetric Synthesis, I. Ojima (ed.), Willey-VCH, New York 2000, rozdz. 5.
[130] R. Noyori, Science, 1990, 248, 1194.
[131] H. Nozaki, S. Moriuti, H. Takaya, R. Noyori, Tetrahedron Lett., 1966, 5239.
[132] X. Yao, M. Qiu, W. Lu, H. Chen, Z. Zheng, Tetrahedron: Asymmetry, 2001, 12, 197.
[133] J.A. Miller, W. Jin, S.T. Nguyen, Angew. Chem., Int. Ed., 2002, 41, 2953.
[134] S.E. Schaus, J. Branalt, E.N. Jacobsen, J. Org. Chem., 1998, 63, 403.
[135] W. Chaładaj, J. Jurczak, Chem. Commun., 2009, 6747.
[136] J.J. Chapman, C.S. Day, M.E. Welker, Eur. J. Org. Chem., 2001, 2273.
[137] Y.N. Belokon, M. North, T.D. Churkina, N.S. Ikonnikov, V.I. Maleev, Tetrahedron, 2001, 57, 2491.
[138] M. North, D. L. Usanov, C. Young, Chem. Rev., 2008, 108, 5146.
[139] V.I. Tararov, D.E. Hibbs, M.B. Hursthouse, N.S. Ikonnikov, K.M.A. Malik, M. North, C. Orizu, Y.N. Belokon, Chem. Commun., 1998, 387.
[140] Y.N. Belokon, N.S. Ikonnikov, M. Moscalenko, M. North, S. Orlova, V.I. Tararov, L. Yashkina, Tetrahedron: Asymmetry, 1996, 7, 851.
[141] M.S. Sigman, E.N. Jacobsen, J. Am. Chem. Soc., 1998, 120, 5315.
[142] B.M. Trost, C. Lee, [w:] Catalytic Asymmetric Synthesis, I. Ojima (ed.), Willey-VCH, New York 2000, rozdz. 8E.
[143] T. Hayashi, Pure Appl. Chem., 1988, 60, 7.
[144] M. Sawamura, Y. Ito, Chem. Rev., 1992, 92, 857.
[145] A. Pfaltz, Acc. Chem. Res., 1993, 26, 339.
[146] B.M. Trost, Acc. Chem. Res., 1996, 29, 355.
[147] B.M. Trost, D.L. van Vranken, C. Bingel, J. Am. Chem. Soc., 1992, 114, 9327.
[148] A. Saitoh, K. Achiwa, K. Tanaka, T. Morimoto, J. Org. Chem., 2000, 65, 4227.
[149] P. Gamez, B. Dunjic, F. Fache, M. Lemaire, Tetrahedron: Asymmetry, 1995, 6, 1109.
[150] B.M. Trost, R.C. Bunt, R. Lemoine, T. Calkins, J. Am. Chem. Soc., 2000, 122, 5968.
[151] B.M. Trost, R. Madsen, S. Guile, Tetrahedron Lett., 1997, 38, 1707.
[152] L. Pu, H.-B. Yu, Chem. Rev., 2001, 101, 757.
[153] H. Takahashi, T. Kawakita, M. Ohno, M. Yoshioka, S. Kobayashi, Tetrahedron, 1992, 48, 5691.
[154] J. Balsells, J.M. Betancort, P.J. Walsh, Angew. Chem., Int. Ed., 2000, 39, 3428.
[155] Enantioselective Organocatalysis: Reactions and Experimental Procedures, Peter I. Dalko (ed.), Wiley-VCH, Weinheim 2007.
[156] M.M. Heravi, S. Asadi, Tetrahedron: Asymmetry, 2012, 23, 1431.
[157] T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc., 2003, 125, 12672.
[158] Y. Hoashi, T. Yabuta, Y. Takemoto, Tetrahedron Lett., 2004, 45, 9185.
[159] Molecular Recognition Mechanisms, M. Delaage (ed.), Wiley-VCH, Weinheim 1999.
[160] J.W. Steed, J.L. Atwood, Supramolecular Chemistry, Wiley-VCH, Weinheim 2009.
[161] S.S. Yoon, W.C. Still, Tetrahedron, 1995, 51, 567.
[162] Z. Pan, W.C. Still, Tetrahedron Lett., 1996, 37, 8699.
[163] I. Alfonso, F. Rebolledo, V. Gotor, Chem. Eur. J., 2000, 6, 3331.
[164] J.L. Sessler, A. Andrievsky, V. Kral, V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385.
[165] J. van Esch, F. Schoonbeek, M. de Loos, H. Kooijman, A.L. Spek, R.M. Kellogg, B.L. Feringa, Chem. Eur. J., 1999, 5, 937.
[166] M. de Loos, J. van Esch, R.M. Kellogg, B.L. Feringa, Angew. Chem., Int. Ed., 2001, 40, 613.
[167] K. Hanabusa, M. Yamada, M. Kimura, H. Shirai, Angew. Chem., Int. Ed., 1996, 35, 1949.
[168] P.H. Hunenberger, J.K. Granwehr, J.-N. Aebischer, N. Ghoneim, E. Haselbach, W.F. van Gunsteren, J. Am. Chem. Soc., 1997, 119, 7533.
[169] S. Hanessian, R. Saladino, R. Margarita, M. Simard, Chem. Eur. J., 1999, 5, 2169.
[170] S. Roelens, P. Dapporto, P. Paoli, Can. J. Chem., 2000, 78, 723.
[171] P. Dapporto, P. Paoli, S. Roelens, J. Org. Chem., 2001, 66, 4930.
[172] M. Sinibaldi, V. Carunchio, C. Corradini, A.M. Girelli, Chromatographia, 1984, 18, 459.
[173] W.H. Pirkle, T.C. Pochapsky, Chem. Rev., 1989, 89, 347.
[174] F. Gasparrini, L. Lunazzi, D. Misiti, C. Villani, Acc. Chem. Res., 1995, 28, 163.
[175] G. Cancelliere, I. D’Acquarica, F. Gasparrini, M. Maggini, D. Misiti, C. Villani, J. Sep. Sci., 2006, 29, 770.
[176] F. Gasparrini, D. Misiti, W.C. Still, C. Villani, H. Wennemers, J. Org. Chem., 1997, 62, 8221.
[177] D. Savoia, A. Gualandi, H. Stoeckli-Evans, Org. Biomol. Chem., 2010, 8, 3992.
[178] A. Gualandi, S. Grilli, D. Savoia, M. Kwit, J. Gawroński, Org. Biomol. Chem., 2011, 9, 4234.
[179] Z. Guo, P.J. Sadler, Angew. Chem., Int. Ed., 1999, 38, 1513.
[180] C. Gao, G. Xu, S. Gou, Bioorg. Med. Chem. Lett., 2011, 21, 6386.
[181] A. Carrato, J. Gallego, E. Diaz-Rubio, Crit. Rev. Oncol. Hematol., 2002, 44, 29.
[182] A. Paraskar, S. Soni, B. Roy, A.-L. Papa, S. Sengupta, Nanotechnology, 2012, 23, 075103.
[182] R. Kowalczyk, P. Kwiatkowski, J. Skarżewski, J. Jurczak, J. Org. Chem., 2009, 74, 753.
[184] W. Chaładaj, P. Kwiatkowski, J. Jurczak, Tetrahedron Lett., 2008, 49, 6810.
[185] P. Kwiatkowski, E. Wojaczyńska, J. Jurczak, J. Mol. Catal. A: Chemical, 2006, 257, 124.
[186] K. Dudziński, A.M. Pakulska, P. Kwiatkowski, Org. Lett., 2012 14, 2864.
[187] R. Kowalczyk, Ł. Sidorowicz, J. Skarżewski, Tetrahedron: Asymmetry, 2008, 19, 2310.
[188] R. Kowalczyk, J. Skarżewski, Tetrahedron: Asymmetry, 2009, 20, 2467.
[189] E. Wojaczyńska, J. Bąkowicz, M. Dorsz, J. Skarżewski, J. Org. Chem., 2013, 78, 2808.
[190] M. Jasiński, G. Mlostoń, P. Mucha, A. Linden, H. Heimgartner, Helv. Chim. Acta, 2007, 90, 1765.
[191] P. Mucha, G. Mlostoń, M. Jasiński, A. Linden, H. Heimgartner, Tetrahedron: Asymmetry, 2008, 19, 1600.
[192] P. Kwiatkowski, P. Mucha, G. Mlostoń, J. Jurczak, Synlett, 2009, 1757.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-8ccc5831-a7c5-45ed-8c43-9b73bba4c510