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Letters in Organic Chemistry

Author(s): Ana Rita G. Félix, Pedro R.D. Simões, Francisco J.P.M. Sousa, M. Elisa Silva Serra and Dina Murtinho*

DOI: 10.2174/2210681209666190807155816

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Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions

Page: [372 - 380] Pages: 9

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Abstract

Several novel chiral organocatalysts derived from thiazolidines containing amide and thioureia functionalities were synthesized in good yields. These organocatalysts were tested in the asymmetric aldol reaction of acetone with p-nitrobenzaldehyde. Reaction parameters such as reaction time, catalyst loading and solvent were optimized. Products with conversions up to 84% and enantiomeric ratios (er) up to 84.5:15.5 (R:S) were obtained. The effect of several chiral and non-chiral additives on the reactivity and selectivity of the reaction was also evaluated. The reaction was extended to other aromatic aldehydes with the best organocatalyst and when p-bromobenzaldehyde was used, an er of 94.5:5.5 (R:S) was obtained.

Keywords: Thiazolidines, organocatalyst, aldol reaction, enantioselective, asymmetric synthesis, additives.

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[1]
Pellissier, H. Tetrahedron, 2007, 63, 9267-9331.
[http://dx.doi.org/10.1016/j.tet.2007.06.024]
[2]
Seayad, J.; List, B. Org. Biomol. Chem., 2005, 3(5), 719-724.
[http://dx.doi.org/10.1039/b415217b] [PMID: 15731852]
[3]
Ricci, A. ISRN Org. Chem., 2014, 1-29.
[http://dx.doi.org/10.1155/2014/531695]
[4]
Gaunt, M.J.; Johansson, C.C.C.; McNally, A.; Vo, N.T. Drug Discov. Today, 2007, 12(1-2), 8-27.
[http://dx.doi.org/10.1016/j.drudis.2006.11.004] [PMID: 17198969]
[5]
Pellissier, H. Adv. Synth. Catal., 2012, 354, 237-294.
[http://dx.doi.org/10.1002/adsc.201100714]
[6]
Hajos, Z.G.; Parrish, D.R. J. Org. Chem., 1974, 39, 1615-1621.
[http://dx.doi.org/10.1021/jo00925a003]
[7]
Moyano, A. Activation modes in asymmetric organocatalysis.Stereoselective Organocatalysis; Torres, R.R., Ed.; John Wiley & Sons, Inc., 2013, pp. 11-80.
[http://dx.doi.org/10.1002/9781118604755.ch02]
[8]
Guillena, G.; Nájera, C.; Ramón, D.J. Tetrahedron Asymmetry, 2007, 18, 2249-2293.
[http://dx.doi.org/10.1016/j.tetasy.2007.09.025]
[9]
Geary, L.M.; Hultin, P.G. Tetrahedron Asymmetry, 2009, 20, 131-173.
[http://dx.doi.org/10.1016/j.tetasy.2008.12.030]
[10]
Yu, N.; Han, S.; Yu, H. Tetrahedron, 2015, 71, 4665-4669.
[http://dx.doi.org/10.1016/j.tet.2015.04.075]
[11]
Gao, Q.; Liu, Y.; Lu, S.; Li, C. Chin. J. Catal., 2011, 32, 899-903.
[http://dx.doi.org/10.1016/S1872-2067(10)60237-9]
[12]
Zhao, W.; Qu, C.; Yang, L.; Cui, Y. Chin. J. Catal., 2015, 36, 367-371.
[http://dx.doi.org/10.1016/S1872-2067(14)60248-5]
[13]
Guo, G.; Wu, Y.; Zhao, X.; Wang, J.; Zhang, L. Tetrahedron Asymmetry, 2016, 27, 740-746.
[http://dx.doi.org/10.1016/j.tetasy.2016.06.014]
[14]
Li, Z-Y.; Chen, Y.; Zheng, C-Q.; Yin, Y.; Wang, L.; Sun, X-Q. Tetrahedron, 2017, 73, 78-85.
[http://dx.doi.org/10.1016/j.tet.2016.11.052]
[15]
Cruz-Hernández, C.; Hernández-González, P.E.; Juaristi, E. Synthesis, 2018, 50, 3445-3459.
[http://dx.doi.org/10.1055/s-0036-1592005]
[16]
List, B.; Lerner, R.A.; Barbas, C.F., III J. Am. Chem. Soc., 2000, 122, 2395-2396.
[http://dx.doi.org/10.1021/ja994280y]
[17]
Liu, J.; Wang, L. Synthesis, 2017, 49, 960-972.
[18]
Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C.F., III J. Am. Chem. Soc., 2001, 123(22), 5260-5267.
[http://dx.doi.org/10.1021/ja010037z] [PMID: 11457388]
[19]
Rambo, R.S.; Schneider, P.H. Tetrahedron Asymmetry, 2010, 21, 2254-2257.
[http://dx.doi.org/10.1016/j.tetasy.2010.07.028]
[20]
Rambo, R.S.; Gross Jacoby, C.; Da Silva, T.L.; Schneider, P.H.; Jacoby, C.G.; Da Silva, T.L.; Schneider, P.H. Tetrahedron Asymmetry, 2015, 26, 632-637.
[http://dx.doi.org/10.1016/j.tetasy.2015.04.010]
[21]
Serra, M.E.S.; Costa, D.; Murtinho, D.; Tavares, N.C.T.; Pinho e Melo, T.M.V.D. Tetrahedron, 2016, 72, 5923-5927.
[http://dx.doi.org/10.1016/j.tet.2016.08.036]
[22]
Zhang, Z.; Bao, Z.; Xing, H. Org. Biomol. Chem., 2014, 12(20), 3151-3162.
[http://dx.doi.org/10.1039/C4OB00306C] [PMID: 24710861]
[23]
Tsakos, M.; Kokotos, C.G. Tetrahedron, 2013, 69, 10199-10222.
[http://dx.doi.org/10.1016/j.tet.2013.09.080]
[24]
He, C.; Ren, X.; Feng, Y.; Chai, Y.; Zhang, S.; Chen, W. Tetrahedron Lett., 2015, 56, 4036-4038.
[http://dx.doi.org/10.1016/j.tetlet.2015.04.119]
[25]
Pratap Reddy Gajulapalli, V.; Lokesh, K.; Vishwanath, M.; Kesavan, V. RSC Advances, 2016, 6, 12180-12184.
[http://dx.doi.org/10.1039/C5RA25025K]
[26]
Pratap Reddy Gajulapalli, V.; Vinayagam, P.; Kesavan, V. Org. Biomol. Chem., 2014, 12(24), 4186-4191.
[http://dx.doi.org/10.1039/c4ob00271g] [PMID: 24824863]
[27]
Li, J.; Yang, G.; Qin, Y.; Yang, X.; Cui, Y. Tetrahedron Asymmetry, 2011, 22, 613-618.
[http://dx.doi.org/10.1016/j.tetasy.2011.03.016]
[28]
Gajulapalli, V.P.R.; Vinayagam, P.; Kesavan, V. RSC Advances, 2015, 5, 7370-7379.
[http://dx.doi.org/10.1039/C4RA13711F]
[29]
Serra-Pont, A.; Alfonso, I.; Solà, J.; Jimeno, C. Org. Biomol. Chem., 2017, 15(31), 6584-6591.
[http://dx.doi.org/10.1039/C7OB01370A] [PMID: 28749514]
[30]
Li, Y.; Yang, Q.; Xu, X-Y.; Zhou, Y.; Bai, J.; Wang, F.; Wang, L.A. Can. J. Chem., 2011, 89, 1312-1318.
[http://dx.doi.org/10.1139/v11-029]
[31]
Da Silva, T.L.; Miolo, L.M.F.; Sousa, F.S.S.; Brod, L.M.P.; Savegnago, L.; Schneider, P.H. Tetrahedron Lett., 2015, 56, 6674-6680.
[http://dx.doi.org/10.1016/j.tetlet.2015.10.037]
[32]
Rojas Cabrera, H.; Huelgas, G.; Hernández Pérez, J.M.; Walsh, P.J.; Somanathan, R.; Anaya De Parrodi, C. Tetrahedron Asymmetry, 2015, 26, 163-172.
[http://dx.doi.org/10.1016/j.tetasy.2015.01.009]
[33]
Xu, B.; Li, L.; Gou, S. Tetrahedron Asymmetry, 2013, 24, 1556-1561.
[http://dx.doi.org/10.1016/j.tetasy.2013.09.026]
[34]
Wang, L.M.; Zhao, M.J.; Chen, Z.; Mu, H.W.; Jin, Y. Chirality, 2018, 30, 1005-1011.
[http://dx.doi.org/10.1002/chir.22977]
[35]
Hong, L.; Sun, W.; Yang, D.; Li, G.; Wang, R. Chem. Rev., 2016, 116(6), 4006-4123.
[http://dx.doi.org/10.1021/acs.chemrev.5b00676] [PMID: 26881289]
[36]
Huang, X-R.; Liu, Q.; Wang, J.; Xiao, J-A.; Yang, H. Tetrahedron Asymmetry, 2014, 25, 1590-1598.
[http://dx.doi.org/10.1016/j.tetasy.2014.10.019]
[37]
Nakashima, K.; Hirashima, S.; Akutsu, H.; Koseki, Y.; Tada, N.; Itoh, A.; Miura, T. Tetrahedron Lett., 2015, 56, 558-561.
[http://dx.doi.org/10.1016/j.tetlet.2014.11.117]
[38]
Eymur, S.; Akceylan, E.; Sahin, O.; Uyanik, A.; Yilmaz, M. Tetrahedron, 2014, 70, 4471-4477.
[http://dx.doi.org/10.1016/j.tet.2014.05.034]
[39]
Naresh, T.; Kumar, T.P.; Haribabu, K.; Chandrasekhar, S. Tetrahedron Asymmetry, 2014, 25, 1340-1345.
[http://dx.doi.org/10.1016/j.tetasy.2014.08.007]
[40]
Kumar, T.P.; Vavle, N.C.; Patro, V.; Haribabu, K. Tetrahedron Asymmetry, 2014, 25, 457-461.
[http://dx.doi.org/10.1016/j.tetasy.2014.01.008]
[41]
Bisticha, A.; Triandafillidi, I.; Kokotos, C.G. Tetrahedron Asymmetry, 2015, 26, 102-108.
[http://dx.doi.org/10.1016/j.tetasy.2014.12.007]
[42]
Vlasserou, I.; Sfetsa, M.; Gerokonstantis, D.T.; Kokotos, C.G.; Moutevelis-Minakakis, P. Tetrahedron, 2018, 74, 2338-2349.
[http://dx.doi.org/10.1016/j.tet.2018.03.054]
[43]
Bhowmick, S.; Mondal, A.; Ghosh, A.; Bhowmick, K.C. Tetrahedron Asymmetry, 2015, 26, 1215-1244.
[http://dx.doi.org/10.1016/j.tetasy.2015.09.009]
[44]
Gryko, D.; Zimnicka, M.; Lipiński, R. J. Org. Chem., 2007, 72(3), 964-970.
[http://dx.doi.org/10.1021/jo062149k] [PMID: 17253817]
[45]
Sutcliffe, O.B.; Storr, R.C.; Gilchrist, T.L.; Rafferty, P. Chem. Soc.Perkin 1,, 2001, 15, 1795-1806.
[46]
Seki, M.; Mori, Y.; Hatsuda, M.; Yamada, S. J. Org. Chem., 2002, 67(16), 5527-5536.
[http://dx.doi.org/10.1021/jo025794+] [PMID: 12153250]
[47]
Tang, Z.; Jiang, F.; Cui, X.; Gong, L-Z.; Mi, A-Q.; Jiang, Y-Z.; Wu, Y-D. Proc. Natl. Acad. Sci. USA, 2004, 101(16), 5755-5760.
[http://dx.doi.org/10.1073/pnas.0307176101] [PMID: 15079057]
[48]
Wagner, M.; Contie, Y.; Ferroud, C.; Revial, G. Int. J. Org. Chem. (Irvine), 2014, 04, 55-67.
[http://dx.doi.org/10.4236/ijoc.2014.41008]