Abstract
Chiral Al/Zn heterobimetallic complexes are effective catalysts for the direct highly enantioselective aldol reaction of acetophenones with aromatic aldehydes. The Al site in the complex acts as a Lewis acid to activate aldehyde, whereas ethylzinc alkoxide plays a role of a Brønsted base to form a reactive zinc enolate with acetophenone. Distinct nature of two different metals contributes to the efficient direct asymmetric aldol reaction.
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Alcaide, B. and Almendros, P. Eur. J. Org. Chem., 2002, p. 1595. doi 10.1002/1099-0690(200205) 2002:10<1595::AID-EJOC1595>3.0.CO;2-M.
Notz, W., Tanaka, F., and Barbas, C.F., III, Acc. Chem. Res., 2004, vol. 37, p. 580. doi 10.1021/ar0300468.
Mukherjee, S., Yang, J.W., Hoffmann, S., and List, B., Chem. Rev., 2007, vol. 107, p. 5471. doi 10.1021/cr0684016.
Shibasaki, M., and Yoshikawa, N., Chem. Rev., 2002, vol. 102, p. 2187. doi 10.1021/cr010297z.
Trost, B.M. and Brindle, C.S., Chem. Soc. Rev., 2010, vol. 39, p. 1600. doi 10.1039/B923537J.
Palomo, C., Oiarbide, M., and García, J.M., Chem. Soc. Rev., 2004, vol. 33, p. 65. doi 10.1039/B202901D.
Modern Aldol Reactions, Mahrwald, R., Ed., Weinheim Wiley-VCH, 2004.
Casiraghi, G., Zanardi, F., Appendino, G., and Rassu, G., Chem. Rev., 2000, vol. 100, p. 1929. doi 10.1021/cr990247i.
Singh, P. and Bhardwaj, A., J. Med. Chem., 2010, vol. 53, p. 3707. doi 10.1021/jm1001327.
Johnson, J.S. and Evans, D.A., Acc. Chem. Res., 2000, vol. 33, p. 325. doi 10.1021/ar960062n.
Mahrwald, R., Chem. Rev., 1999, vol. 99, p. 1095. doi 10.1021/cr980415r.
Gröger, H., Vogl, E.M., and Shibasaki, M., Chem. Eur. J., 1998, vol. 4, p. 1137. doi 10.1002/(SICI)1521-3765(19980710)4:7<1137:: AID-CHEM1137>3.0.CO;2-Z.
Nelson, S.G., Tetrahedron: Asymmetry, 1998, vol. 9, p. 357. doi 10.1016/S0957-4166(97)00634-4.
Li, H.-J., Tian, H.-Y., Wu, Y.-C., Chen, Y.-J., Liu, L., Wang, D. and Li, C.-J., Adv. Synth. Catal., 2005, vol. 347, p. 1247. doi 10.1002/adsc.200505089.
Mlynarski, J. and Jankowska, J., Adv. Synth. Catal., 2005, vol. 347, p. 521. doi 10.1002/adsc.200404314.
Denmark, S.E. and Heemstra, J.R., Org. Lett., 2003, no. 5, p. 2303. doi 10.1021/ol034641l.
Kiyooka, S., Takeshita, Y., Tanaka, Y., Higaki, T., and Wada, Y., Tetrahedron Lett., 2006, vol. 47, p. 4453. doi 10.1016/j.tetlet.2006.04.068.
Li, H.-J., Tian, H.-Y., Chen, Y.-J., Wang, D., and Li, C.-J., Chem. Commun., 2002, p. 2994. doi 10.1039/B208411B.
Zhao, J.-F., Tan, B.-H., and Loh, T.-P., Chem. Sci., 2011, p. 349. doi 10.1039/C0SC00454E.
Yu, J., Zhao, X., Miao, Z., and Chen, R., Org. Biomol. Chem., 2011, p. 6721. doi 10.1039/C1OB05822C.
Yamada, Y.M.A., Yoshikawa, N., Sasai, H., and Shibasaki, M., Angew. Chem. Int. Ed., 1997, vol. 36, p. 1871. doi 10.1002/anie.199718711.
Yoshikawa, N., Yamada, Y.M.A., Das, J., Sasai, H., and Shibasaki, M., J. Am. Chem. Soc., 1999, vol. 121, p. 4168. doi 10.1021/ja990031y.
Yoshikawa, N., Kumagai, N., Mutsunaga, S., Moll, G., Ohshima, T., Suzuki, T., and Shibasaki, M., J. Am. Chem. Soc., 2001, vol. 123, p. 2466. doi 10.1021/ja015580u.
Kumagai, N., Matsunaga, S., Yoshikawa, N., Ohshima, T., and Shibasaki, M., Org. Lett., 2001, p. 1539. doi 10.1021/ol015878p.
Trost, B.M. and Ito, H., J. Am. Chem. Soc., 2000, vol. 122, p. 12003. doi 10.1021/ja003033n.
Trost, B.M., Ito, H., and Silcoff, E.R., J. Am. Chem. Soc., 2001, vol. 123, p. 3367. DOI:10.1021/ja003871h.
Trost, B.M. and Yeh, V.S.C., Angew. Chem. Int. Ed., 2002, vol. 41, p. 861. doi 10.1002/1521-3773(20020301) 41:5<861::AID-ANIE861>3.0.CO;2-V.
Trost, B.M. and Mino, T., J. Am. Chem. Soc., 2003, vol. 125, p. 2410. doi 10.1021/ja029708z.
Trost, B.M. and Terrell, L.R., J. Am. Chem. Soc., 2003, vol. 125, p. 338. doi 10.1021/ja028782e.
Trost, B.M., Fettes, A., and Shireman, B.T., J. Am. Chem. Soc., 2004, vol. 126, p. 2660. doi 10.1021/ja038666r.
Trost, B.M., Weiss, A.H., and von Wanggelin, A.J., J. Am. Chem. Soc., 2005, vol. 128, p. 8. doi 10.1021/ja054871q.
Trost, B.M., Shin, S., and Sclafani, J.A., J. Am. Chem. Soc., 2005, vol. 127, p. 8602. doi 10.1021/ja051526s.
Li, H., Da, C.-S., Xiao, Y.-H., Li, X., and Su, Y.N., J. Org. Chem., 2008, vol. 73, p. 7398. doi 10.1021/jo801182n.
Shibasaki, M., Sasai, H., and Arai, T., Angew. Chem. Int. Ed., 1997, vol. 36, p. 1236. doi 10.1002/anie.199712361.
Shibasaki, M. and Gröger, H., Top Organomet. Chem., 1999, p. 199.
Shibasaki, M. and Yoshikawa, N., Chem. Rev., 2002, vol. 102, p. 2187. doi 10.1021/cr010297z.
Shibasaki, M., Kanai, M., Matsunaga, S., and Kumagai, N., Acc. Chem. Res., 2004, vol. 37, p. 580. doi 10.1021/ar0300468.
Matsunaga, S. and Shibasaki, M., Bull. Chem. Soc. Japan, 2008, vol. 81, p. 60. doi 10.1246/bcsj.81.60.
Mihara, H., Xu, Y., Sheperd, N.E., Matsunaga, S., and Shibasaki, M., J. Am. Chem. Soc., 2009, vol. 131, p. 8384. doi 10.1021/ja903158x.
Handa, S., Gnanadesikan, V., Matsunaga, S., and Shibasaki, M., J. Am. Chem. Soc., 2010, vol. 132, p. 4925. doi 10.1021/ja100514y.
Iwata, M., Yazaki, R., Chen, I.-H., Sureshkumar, D., Kumagai, N., and Shibasaki, M., J. Am. Chem. Soc., 2011, vol. 133, p. 5554. doi 10.1021/ja200250p.
Donets, P.A. and Cramer, N., J. Am. Chem. Soc., 2013, vol. 135, p. 11772. doi 10.1021/ja406730t.
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Li, X., Zhang, L., Xiao, YH. et al. Direct asymmetric aldol reaction of acetophenones with aromatic aldehydes catalyzed by chiral Al/Zn heterobimetallic compounds. Russ J Gen Chem 86, 1922–1930 (2016). https://doi.org/10.1134/S1070363216080247
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DOI: https://doi.org/10.1134/S1070363216080247