Abstract
Chiral norephedrine-based β-amino alcohol bearing a substituted thiophene ring were applied as catalysts for the enantioselective aldol reaction of isatins with ketones. Using enantiomeric chiral amino alcohols, the desired aldol products were obtained in high yields and excellent enantioselectivities (up to 95% ee) under optimized conditions.
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REFERENCES
Alcaide, B. and Almendros, P., Angew. Chem., Int. Ed., 2003, vol. 42, p. 858. https://doi.org/10.1002/anie.200390232
Allemann, C., Gordillo, R., Clemente, F.R., Cheong, P.H.-Y., and Houk, K.N., Acc. Chem. Res., 2004, vol. 37, p. 558. https://doi.org/10.1021/ar0300524
Saito, S. and Yamamoto, H., Acc. Chem. Res., 2004, vol. 37, p. 570. https://doi.org/10.1021/ar030064p
List, B., Acc. Chem. Res., 2004, vol. 37, p. 548. https://doi.org/10.1021/ar0300571
Peddibhotla, S., Curr. Bioact. Compd., 2009, vol. 5, p. 20. https://doi.org/10.2174/157340709787580900
Bisai, V., Bisai, A., and Singh, V.K., Tetrahedron, 2012, vol. 68, p. 4541. https://doi.org/10.1016/j.tet.2012.03.099
Kamano, Y., Zhang, H.-P., Ichihara, Y., Kizu, H., Komiyama, K., and Pettit, G.R., Tetrahedron Lett., 1995, vol. 36, p. 2783. https://doi.org/10.1016/0040-4039(95)00395-S
Miah, S., Moody, C.J., Richards, I.C., and Slawin, A.M.Z., J. Chem. Soc., Perkin Trans. 1, 1997, p. 2405. https://doi.org/10.1039/A700683G
Nicolaou, K.C., Huang, X., Giuseppone, N., Rao, P.B., Bella, M., Reddy, M.V., and Snyder, S.A., Angew. Chem., Int. Ed., 2001, vol. 40, p. 4705. https://doi.org/10.1002/1521-3773(20011217)40:24<4705::AID-ANIE4705>3.0.CO;2-D
Nicolaou, K.C., Chen, D.Y.-K., Huang, X.H., Ling, T., Bella, M., and Snyder, S.A., J. Am. Chem. Soc., 2004, vol. 126, p. 12888. https://doi.org/10.1021/ja040092i
Nicolaou, K.C., Rao, P.B., Hao, J.L., Reddy, M.V., Rassias, G., Huang, X.H., Chen, D.Y.-K., and Snyder, S.A., Angew. Chem., Int. Ed., 2003, vol. 42, p. 1753. https://doi.org/10.1002/anie.200351112
Nicolaou, K.C., Snyder, S.A., Giuseppone, N., Huang, X., Bella, M., Reddy, M.V., Rao, P.B., Koumbis, A.E., Giannakakou, P., and O’Brate, A., J. Am. Chem. Soc., 2004, vol. 126, p. 10174. https://doi.org/10.1021/ja040091q
Takahashi, C., Numata, A., Ito, Y., Matsumura, E., Araki, H., Iwaki, H., and Kushida, K., J. Chem. Soc., Perkin Trans. 1, 1994, p. 1859. https://doi.org/10.1039/P19940001859
Fréchard, A., Fabre, N., Péan, C., Montaut, S., Fauvel, M.-T., Rollin, P., and Fourasté, I., Tetrahedron Lett., 2001, vol. 42, p. 9015. https://doi.org/10.1016/S0040-4039(01)02015-9
Jimenez, J.I., Huber, U., Moore, R.E., and Patterson, G.M.L., J. Nat. Prod., 1999, vol. 62, p. 569. https://doi.org/10.1021/np980485t
Feldman, K.S. and Karatjas, A.G., Org. Lett., 2004, vol. 6, p. 2849. https://doi.org/10.1021/ol048974+
Lin, S., Yang, Z.-Q., Kwok, B.H.B., Koldobskiy, M., Crews, C.M., and Danishefsky, S.J., J. Am. Chem. Soc., 2004, vol. 126, p. 6347. https://doi.org/10.1021/ja049821k
Albrecht, B.K. and Williams, R.M.A., Org. Lett., 2003, vol. 5, p. 197. https://doi.org/10.1021/ol0272545
Suzuki, H., Morita, H., Shiro, M., and Kobayashi, J., Tetrahedron, 2004, vol. 60, p. 2489. https://doi.org/10.1016/j.tet.2004.01.053
Suchý, M., Kutschy, P., Monde, K., Goto, H., Harada, N., Takasugi, M., Dzurilla, M., and Balentova, E., J. Org. Chem., 2001, vol. 66, p. 3940. https://doi.org/10.1021/jo0155052
Kumar, R.R. and Perumal, S., Tetrahedron, 2007, vol. 63, p. 12220. https://doi.org/10.1016/j.tet.2007.09.033
Franz, A.K., Dreyfuss, P.D., and Schreiber, S.L., J. Am. Chem. Soc., 2007, vol. 129, p. 1020. https://doi.org/10.1021/ja067552n
Schulz, V., Davoust, M., Lemarié, M., Lohier, J.-F., Oliveira Santos, J.S., Metzner, P., and Brière, J.-F., Org. Lett., 2007, vol. 9, p. 1745. https://doi.org/10.1021/ol070439x
Luppi, G., Cozzi, P.G., Monari, M., Kaptein, B., Broxterman, Q.B., and Tomasini, C., J. Org. Chem., 2005, vol. 70, p. 7418. https://doi.org/10.1021/jo050257l
Kinsella, M., Duggan, P.G., and Lennon, C.M., Tetrahedron: Asymmetry, 2011, vol. 22, p. 1423. https://doi.org/10.1016/j.tetasy.2011.07.016
Chen, J.R., Liu, X.P., Zhu, X.Y., Li, L., Qiao, Y.F., Zhang, J.M., and Xiao, W.J., Tetrahedron, 2007, vol. 63, p. 10437. https://doi.org/10.1016/j.tet.2007.08.003
Pearson, A.J. and Panda, S., Org. Lett., 2011, vol. 13, p. 5548. https://doi.org/10.1021/ol202284n
Itoh, T., Ishikawa, H., and Hayashi, Y., Org. Lett., 2009, vol. 11, p. 3854. https://doi.org/10.1021/ol901432a
Prathima, P.S., Srinivas, K., Balaswamy, K., Arundhathi, R., Reddy, G.N., Sridhar, B., Rao, M.M., and Likhar, P.R., Tetrahedron: Asymmetry, 2011, vol. 22, p. 2099. https://doi.org/10.1021/ol901432a
Guo, Q.S., Bhanushali, M., and Zhao, C.-G., Angew. Chem., Int. Ed., 2010, vol. 49, p. 9460. https://doi.org/10.1002/anie.201004161
Ogasawara, A., Reddy, U.V.S., Seki, C., Okuyama, Y., Uwai, K., Tokiwa, M., Takeshita, M., and Nakano, H., Tetrahedron: Asymmetry, 2016, vol. 27, p. 1062. https://doi.org/10.1016/j.tetasy.2016.08.013
Allu, S., Molleti, N., Panem, R., and Singh, V.K., Tetrahedron Lett., 2011, vol. 52, p. 4080. https://doi.org/10.1016/j.tetlet.2011.05.013
Bañón-Caballero, A., Flores-Ferrándiz, J., Guillena, G., and Nájera, C., Molecules, 2015, vol. 20, p. 12901. https://doi.org/10.3390/molecules200712901
Shen, C., Shen, F., Xia, H., Zhang, P., and Chen, X., Tetrahedron: Asymmetry, 2011, vol. 22, p. 708. https://doi.org/10.1016/j.tetasy.2011.04.007
Chen, G., Ju, Y., Yang, T., Li, Z., Ang, W., Sang, Z., Liu, J., and Luo, Y., Tetrahedron: Asymmetry, 2015, vol. 26, p. 943. https://doi.org/10.1016/j.tetasy.2015.07.008
Kabeshov, M.A., Kysilka, O., Rulíšek, L., Suleimanov, Y.V., Bella, M., Malkov, A.V., and Kočovský, P., Chem. Eur. J., 2015, vol. 21, p. 12026. https://doi.org/10.1002/chem.201500536
Malkov, A.V., Kabeshov, M.A., Bella, M., Kysilka, O., Malyshev, D.A., Pluháčkova, K., and Kočovský, P., Org. Lett., 2007, vol. 9, p. 5473. https://doi.org/10.1021/ol7023983
Aydin, A.E., Appl. Organomet. Chem., 2013, vol. 27, p. 283. https://doi.org/10.1002/aoc.2969
Aydin, A.E., Tetrahedron: Asymmetry, 2013, vol. 24, p. 444. https://doi.org/10.1016/j.tetasy.2013.03.011
Aydin, A.E., Russ. J. Org. Chem., 2020, vol. 56, no. 5, p. 901. https://doi.org/10.1134/S1070428020050255
Yadav, G.D. and Singh, S., Tetrahedron: Asymmetry, 2016, vol. 27, p. 123. https://doi.org/10.1016/j.tetasy.2015.12.005
Mohammadi, S., Heiran, R., Herrera, R.P., and Marqués-López E., ChemCatChem, 2013, vol. 5, p. 2131. https://doi.org/10.1002/cctc.201300050
Zhong, F., Yao, W., Dou, X., and Lu, Y., Org. Lett., 2012, vol. 14, no. 15, p. 4018. https://doi.org/10.1021/ol301855w
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Aydin, A.E. Enantioselective Aldol Reaction between Isatins and Ketones, Catalyzed by Chiral Norephedrine-Derived β-Amino Alcohols with a Thiophene Moiety. Russ J Org Chem 58, 820–829 (2022). https://doi.org/10.1134/S1070428022060100
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DOI: https://doi.org/10.1134/S1070428022060100