Abstract
Chiral oxazoline ligands containing an aromatic ring were prepared from norephedrine and pyrrole-2-carbonitrile or 2-hydroxybenzoyl chloride. The synthesized ligands were used in the copper-catalyzed asymmetric addition of diethylzinc to aromatic aldehydes to provide optically active 1-arylpropan-1-ols with high conversion (92%) and enantioselectivity (up to 99% ee).
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REFERENCES
Pu, L. and Yu, H.B., Chem. Rev., 2001, vol. 101, p. 757. https://doi.org/10.1021/cr000411y
Duthaler, R.O. and Hafner, A., Chem. Rev., 1992, vol. 92, p. 807. https://doi.org/10.1021/cr00013a003
Bauer, T. and Smoliński, S., Appl. Catal. A: Gen., 2010, vol. 375, p. 247. https://doi.org/10.1016/j.apcata.2010.01.009
Luderer, M.R., Bailey, W.F., Luderer, M.R., Fair, J.D., Dancer, R.J., and Sommer, M.B., Tetrahedron: Asymmetry, 2009, vol. 20, p. 981. https://doi.org/10.1016/j.tetasy.2009.03.015
Noyori, R. and Kitamura, M., Angew. Chem., Int. Ed., 1991, vol. 30, p. 49. https://doi.org/10.1002/anie.199100491.
Hatano, M., Miyamoto, T., and Ishihara, K., Curr. Org. Chem., 2007, vol. 11, p. 127. https://doi.org/10.2174/138527207779316453
Knochel, P. and Singer, R.D., Chem. Rev., 1993, vol. 93, p. 2117. https://doi.org/10.1021/cr00022a008
Noyori, R., Asymmetric Catalysis in Organic Synthesis, New York: Wiley, 1994.
Soai, K. and Niwa, S., Chem. Rev., 1992, vol. 92, p. 833. https://doi.org/10.1021/cr00013a004
Pisani, L., Superchi, S., D’Elia, A., Scafato, P., and Rosini, C.,Tetrahedron, 2012, vol. 68, p. 5779. https://doi.org/10.1016/j.tet.2012.05.028
Kim, H.Y. and Walsh, P.J., J. Phys. Org. Chem., 2012, vol. 25, p. 933. https://doi.org/10.1002/poc.2965
González-López, S., Yus, M., and Ramón, D., Tetrahedron: Asymmetry, 2012, vol. 23, p. 611. https://doi.org/10.1016/j.tetasy.2012.04.003
Panda, M., Phuan, P.W., and Kozlowski, M.C., J. Org. Chem., 2003, vol. 68, p. 564. https://doi.org/10.1021/jo0262210
Bian, G., Huang, H., Zong, H., and Song, L., Chirality, 2012, vol. 24, p. 825. https://doi.org/10.1002/chir.22078
Olsson, C., Helgesson, S., and Frejd, T., Tetrahedron: Asymmetry, 2008, vol. 19, p. 1484. https://doi.org/10.1016/j.tetasy.2008.06.002
Martinez, A.G., Vilar, E.T., Fraile, A.G., Cerero, S.D., and Maroto, B.L., Tetrahedron, 2005, vol. 61, p. 3055. https://doi.org/10.1016/j.tet.2005.01.108
Yang, X.F., Wang, Z.H., Koshizawa, T., Yasutake, M., Zhang, G.Y., and Hirose, T., Tetrahedron: Asymmetry, 2007, vol. 18, p. 1257. https://doi.org/10.1016/j.tetasy.2007.05.027
Szatmári, I., Siillanpää, R., and Fülöp, F., Tetrahedron: Asymmetry, 2008, vol. 19, p. 612. https://doi.org/10.1016/j.tetasy.2008.01.025
Conti, S., Falorni, M., Giacomelli, G., and Soccolini, F.,Tetrahedron, 1992, vol. 48, p. 8993. https://doi.org/10.1016/S0040-4020(01)81997-9
Niwa, S. and Soai, K., J. Chem. Soc., Perkin. Trans. 1, 1991, no. 28, p. 2717. https://doi.org/10.1039/P19910002717
Martins, J.E.D. and Wills, M., Tetrahedron: Asymmetry, 2008, vol. 19, p. 1250. https://doi.org/10.1016/j.tetasy.2008.04.020
Cernerud, M., Skrinning, A., Bérgère, I., and Moberg, C., Tetrahedron: Asymmetry, 1997, vol. 8, p. 3437. https://doi.org/10.1016/S0957-4166(97)00410-2
Paquette, L.A. and Zhou, R., J. Org. Chem., 1999, vol. 64, p. 7929. https://doi.org/10.1021/jo990984e
Grach, G., Reboul, V., and Metzner, P., Tetrahedron: Asymmetry, 2008, vol. 19, p. 1744. https://doi.org/10.1016/j.tetasy.2008.06.031
Kostova, K., Genov, M., Philipova, I., and Dimitrov, V., Tetrahedron: Asymmetry, 2000, vol. 11, p. 3253. https://doi.org/10.1016/S0957-4166(00)00291-3
Liu, B., Dong, Z.B., Fang, C., Song, H.B., and Li, J.S., Chirality, 2008, vol. 20, p. 828. https://doi.org/10.1002/chir.20559
Nakamura, Y., Takeuchi, S., Ohgo, Y., and Curran, D.P., Tetrahedron Lett., 2000, vol. 1, p. 57. https://doi.org/10.1016/S0040-4039(99)01999-1
Mamaghani, M., Mahmoodi, N.O., and Ghasemi, S.F., J. Iran. Chem. Soc., 2010, vol. 7, p. 972. https://doi.org/10.1007/BF03246093
Saeed, A. and Young, D.W., Tetrahedron, 1992, vol. 48, p. 2507. https://doi.org/10.1016/S0040-4020(01)88770-6
Greene, T.W. and Wutz, P.G.M., Protective Groups in Organic Synthesis, NewYork: Wiley, 1991, 2nd ed.
Chaudhry, P., Schoenen, F., Neuenswander, B., Lushington, G.H., and Aubé, J., J. Comb. Chem. 2007, vol. 9, p. 473. https://doi.org/10.1021/cc060159t
Fernández, A.I., Fraile, J.M., Garcia, J.L., Mayoral, J.A., and Salvatella, L., Catal. Commun., 2001, vol. 2, p. 165. https://doi.org/10.1016/S1566-7367(01)00027-9
Lee, A., Kim, W., Lee, J., Hyeon, T., and Kim, B.M., Tetrahedron: Asymmetry, 2004, vol. 15, p. 2595. https://doi.org/10.1016/j.tetasy.2004.07.024
Lu, S.F., Du, D.-M., Zhang, S.W., and Xu, J., Tetrahedron: Asymmetry, 2004, vol. 15, p. 3433. https://doi.org/10.1016/j.tetasy.2004.09.011
Hallaman, K., Macedo, E., Nordtro, M.K., and Moberg, C., Tetrahedron: Asymmetry, 1999, vol. 10, p. 4037. https://doi.org/10.1016/S0957-4166(99)00416-4
Brunner, H., Störiko, R., and Nuber, B., Tetrahedron: Asymmetry, 1998, vol. 9, p. 407. https://doi.org/10.1016/S0957-4166(97)00619-8
Risgaard, T., Gothelf, K.V., and Jørgensen, K.A., Org. Biomol. Chem., 2003, vol. 1, p. 153. https://doi.org/10.1039/B208859M
Schinnerl, M., Bolm, C., Seitz, M., and Reiser, O., Tetrahedron: Asymmetry, 2003, vol. 14, p. 765. https://doi.org/10.1016/S0957-4166(03)00094-6
Johnson, J.S. and Evans, D.A., Acc. Chem. Res., 2000, vol. 33, p. 325. https://doi.org/10.1021/ar960062n
Ghosh, A.K., Mathivanan, P., Capiello, P.J., Tetrahedron: Asymmetry, 1998, vol. 9, p. 1. https://doi.org/10.1016/S0957-4166(97)00593-4
Du, D.M., Lu, S., Fang, F.T., and Xu, J.X., J. Org. Chem., 2005, vol. 70, p. 3712. https://doi.org/10.1021/jo050097d
Christensen, C., Julh, K., and Jørgensen, K.A., Chem. Commun., 2001, p. 2222. https://doi.org/10.1039/B105929G
Evans, D.A., Seidel, D., Rueping, M., Lam, H.W., Shaw, J.T., and Downey, C.W., J. Am. Chem. Soc., 2003, vol. 125, p. 12692. https://doi.org/10.1021/ja0373871
Li, W.J., Xu, Z.L., and Qiu, S.X., Beilstein J. Org. Chem., 2010, vol. 6, p. 1. https://doi.org/10.3762/bjoc.6.29
Kodama, H., Ito, J., Hori, K., Ohta, T., and Furukawa, I.,J. Organomet. Chem., 2000, vol. 600, p. 6. https://doi.org/10.1016/S0022-328X(00)00024-3
Yang, W. and Du, D.M., Eur. J. Org. Chem., 2011, vol. 2011, no. 8, p. 1552. https://doi.org/10.1002/ejoc.201001587
Liu, D.L., Dai, Q., and Zhang, Z., Tetrahedron, 2005, vol. 61, p. 6460. https://doi.org/10.1016/j.tet.2005.03.111
Guiry, P.J. and Saunders, C.P., Adv. Synth. Catal., 2004, vol. 346, p. 497. https://doi.org/10.1002/adsc.200303138
Chelucci, G., Orru, G., and Pinna, G.A., Tetrahedron, 2003, vol. 59, p. 9471. https://doi.org/10.1016/j.tet.2003.09.066
Helmchen, G. and Pfaltz, G.A., Acc. Chem. Res., 2000, vol. 33, p. 336. https://doi.org/10.1021/ar9900865
Fache, F., Schulz, E., Tommasino, M.L., and Lemaire, M., Chem. Rev., 2000, vol. 100, p. 2159. https://doi.org/10.1021/cr9902897
Nishibayashi, Y., Singh, J.D., Segawa, K., Fukuzawa, S.I., and Uemura, S., J. Chem. Soc., Chem. Commun., 1994, p. 1375. https://doi.org/10.1039/C39940001375
Nishibayashi, Y., Segawa, K., Singh, J.D., Fukuzawa, S.I., Ohea, K., and Uemura, S., Organometallics, 1996, vol. 15, p. 370. https://doi.org/10.1021/om950533u
Chelucci, G., Sanna, G.M., and Gladiali, S., Tetrahedron, 2000, vol. 56, p. 2889. https://doi.org/10.1016/S0040-4020(00)00144-7
Dawson, G., Frost, J.C.G., and Williams, J.M.J., Tetrahedron Lett., 1993, vol. 34, p. 3149. https://doi.org/10.1016/S0040-4039(00)93403-8
Braga, A.L., Lüdtke, D.S., and Alberto, E.E., J. Braz. Chem. Soc., 2006, vol. 17, p. 11. https://doi.org/10.1590/S0103-50532006000100002
Qi, M.-H., Wang, F.-J., and Shi, M., Tetrahedron: Asymmetry, 2010, vol. 21, p. 247. https://doi.org/10.1016/j.tetasy.2010.02.003
Noel, T., Robeyns, K., Meervelt, L.V., Eycken, E.V., and Eycken, V.J.V., Tetrahedron: Asymmetry, 2009, vol. 20, p. 1962. https://doi.org/10.1016/j.tetasy.2009.07.038
Wirth, T., Tetrahedron Lett., 1995, vol. 36, p. 7849. https://doi.org/10.1016/0040-4039(95)01668
Allen, J.V., Frost, C.G., and Williams, J.M.J., Tetrahedron: Asymmetry, 1993, vol. 4, p. 649. https://doi.org/10.1016/S0957-4166(00)80170-6
Braga, A.L., Paixäo, M.W., Lüdtke, D., Silveira, S.C., and Rodrigues, O.E.D., Org. Lett., 2003, vol. 5, p. 2635. https://doi.org/10.1021/ol034773e
Park, J., Lang, K., Abboud, K.A., and Hong, S., J. Am. Chem. Soc., 2008, vol. 130, p. 16484. https://doi.org/10.1021/ja807221s
Spangler, K.Y. and Wong, C., Org. Lett., 2009, vol. 11, p. 4724. https://doi.org/10.1021/ol9018612
Sandeep, K. and Singh, V.K., Org. Biomol. Chem., 2007, vol. 5, p. 3932. https://doi.org/10.1039/B714153J
Yang, W., Liu, H., and Du, D.-M., Org. Biomol. Chem., 2010, vol. 8, p. 2956. https://doi.org/10.1039/B923835B
Toussaint, A. and Pfaltz, A., Eur. J. Org. Chem., 2008, vol. 2008, p. 4591. https://doi.org/10.1002/ejoc.200800570
Brunner, H. and Haßler, B.Z., Z. Naturforsch., B: J. Chem. Sci., 1998, vol. 53, p. 476.
Brunner, H. and Haßler, B.Z., Z. Naturforsch., B: J. Chem. Sci., 1998, vol. 53, p. 126.
Aydin, A.E. and Yuksekdanaci, S., Tetrahedron: Asymmetry, 2013, vol. 24, p. 14. https://doi.org/10.1016/j.tetasy.2012.11.022
Pastor, I.M. and Adolfsson, H., Tetrahedron Lett., 2002, vol. 43, p. 1743. https://doi.org/10.1016/S0040-4039(02)00087-4
Bauer, M. and Kazmaier, U., J. Organomet. Chem., 2006, vol. 691, p. 2155. https://doi.org/10.1016/j.jorganchem.2005.10.048
Bolm, C., Zani, L., Rudolph, J., and Schiffers, I., Synthesis, 2004, vol. 2004, p. 2173. https://doi.org/10.1055/s-2004-829184
Zhang, X.M., Zhang, H.L., Lin, W.Q., Gong, L.Z., Mi, A., Cui, Q.X., Jiang, Y.Z., and Yu, K.B., J. Org. Chem., 2003, vol. 68, p. 4322. https://doi.org/10.1021/jo0268862
Bolm, C., Muñiz Fernández, K., Seger, A., and Raabe, G., Synlett, 1997, vol. 1997, p. 1051. https://doi.org/10.1055/s-1997-1528
Schinner, M., Seitz, M., Kaiser, A., and Reiser, O., Org. Lett., 2001, vol. 3, p. 4259. https://doi.org/10.1021/ol016925g
Blay, G., Fernández, I., Marco-Aleixandre, A., and Pedro, J.R.,Tetrahedron: Asymmetry, 2005, vol. 16, p. 1207. https://doi.org/10.1016/j.tetasy.2005.01.039
Dai, W.-M., Zhu, H.-J., and Hao, X.-J., Tetrahedron: Asymmetry, 2000, vol. 11, p. 2315. https://doi.org/10.1016/S0957-4166(00)00189-0
Yang, X.-F., Hirose, T., and Zhang, G.-Y., Tetrahedron: Asymmetry, 2008, vol. 19, p. 1670. https://doi.org/10.1016/j.tetasy.2008.06.027
Shen, X., Guo, H., and Ding, K., Tetrahedron:Asymmetry, 2000, vol. 11, p. 4321. https://doi.org/10.1016/S0957-4166(00)00413-4
Zong, H., Huang, H., Bian, G., and Song, L., Tetrahedron Lett., 2013, vol. 54, p. 2722. https://doi.org/10.1016/j.tetlet.2013.03.066
Hayashi, M., Kaneko, T., and Ogani, N., J. Chem. Soc., Perkin. Trans. 1, 1991, p. 25. https://doi.org/10.1039/P19910000025
Yang, W.K. and Cho, B.T., Tetrahedron: Asymmetry, 2000, vol. 11, p. 2947. https://doi.org/10.1016/S0957-4166(00)00253-6
Shen, B., Huang, H., Bian, G., Zong, H., and Song, L., Chirality, 2013, vol. 25, p. 561. https://doi.org/10.1002/chir.22171
Lin, R.X. and Chen, C., J. Mol. Catal. A: Chem., 2006, vol. 243, p. 89. https://doi.org/10.1016/j.molcata.2005.07.047
Gou, S., Ye, Zh., Gou, G., and Feng, M., Appl. Organomet. Chem., 2011, vol. 25, p. 110. https://doi.org/10.1002/aoc.1724
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This research (1005M0115) is financially supported by the Scientific Research Commission of Mustafa Kemal University.
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Aydin, A.E. Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Chiral Oxazoline-Based Ligands. Russ J Org Chem 56, 1304–1312 (2020). https://doi.org/10.1134/S1070428020070271
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DOI: https://doi.org/10.1134/S1070428020070271