Artículos de revistas
Asymmetric Reduction Of Prochiral Ketones Using In Situ Generated Oxazaborolidine Derived From (1s,2s,3r,4r)-3-amino-7,7-dimethoxynorbornan-2-ol. An Efficient Synthesis Of Enantiopure (r)-tomoxetine
Registro en:
Tetrahedron Letters. , v. 46, n. 3, p. 495 - 498, 2005.
404039
10.1016/j.tetlet.2004.11.052
2-s2.0-11144284669
Autor
Lapis A.A.M.
De Fatima A.
Martins J.E.D.
Costa V.E.U.
Pilli R.A.
Institución
Resumen
In this work, we report our results on the asymmetric reduction of prochiral aromatic and aliphatic ketones 3, 5-8 catalyzed by the novel in situ generated oxazaborolidine 2 derived from (1S,2S,3R,4R)-3-amino-7,7- dimethoxybornan-2-ol (1) and BH 3•Me 2S. This methodology was applied to the synthesis of the anti-depressant drug (R)-tomoxetine in three steps and 47% overall yield from 3-chloropropiophenone (3h). Catalytic asymmetric reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalyst 2 prepared in situ from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorbornan-2-ol (1). The optically active secondary alcohols were generally obtained in moderate to high enantiomeric excesses (ee 43-95%) and good yields (75-94%), except for ketones bearing electron-withdrawing groups. The methodology was applied to the synthesis of enantiopure (R)-tomoxetine, a potent anti-depressant drug. © 2004 Elsevier Ltd. All rights reserved. 46 3 495 498 Noyori, R., (1994) Asymmetric Catalysis in Organic Synthesis, , John Wiley & Sons New York Ojima, I., (1993) Catalytic Asymmetric Synthesis, , VHC Berlin Itsuno, S., Ito, K., Hirao, A., Nakahama, S., (1983) J. Chem. Soc., Chem. Commun., pp. 469-470 Corey, E.J., Bakshi, R.K., Shibata, S., (1987) J. Am. Chem. Soc., 109, pp. 5551-5553 Corey, E.J., Helal, C.J., (1998) Angew. Chem., Int. Ed., 37, pp. 1987-2012 Deloux, L., Srebnik, M., (1993) Chem. Rev., 93, pp. 763-784 Martens, J., Wallbaum, S., (1992) Tetrahedron: Asymmetry, 3, pp. 1475-1504 Mathre, D.J., Thompson, A.S., Douglas, A.W., Hoogsteen, K., Carroll, J.D., Corley, E.G., Grabowski, E.J.J., (1993) J. Org. Chem., 58, pp. 2880-2888 Quallich, G.J., Woodall, T.M., (1993) Synlett, pp. 929-930 Jiang, B., Feng, Y., Hang, J.F., (2001) Tetrahedron: Asymmetry, 12, pp. 2323-2329 Brunin, T., Cabou, J., Bastin, S., Brocard, J., Pelinski, L., (2002) Tetrahedron: Asymmetry, 13, pp. 1241-1243 Zhou, H., Lü, S., Xie, R., Chan, A.S.C., Yang, T.-K., (2001) Tetrahedron Lett., 42, pp. 1107-1110 Lapis, A.A.M., Kreutz, O.C., Pohlmann, A.R., Costa, V.E.U., (2001) Tetrahedron: Asymmetry, 12, pp. 557-561 Zerbe, R.L., Rowe, H., Enas, G.G., Wong, D., Farid, N., Lemberger, L., (1985) J. Pharmacol. Exp. Ther., 232, pp. 139-143 Kamal, A., Khanna, G.B.R., Ramu, R., (2002) Tetrahedron: Asymmetry, 13, pp. 2039-2051 Bymaster, F.P., Katner, J.S., Nelson, D.L., Hemrick-Luecke, S.K., Threlkeld, P.G., Heiligenstein, J.H., Morin, S.M., Perry, K.W., (2002) Neuropsychopharmacology, 27, pp. 699-711 Prasad, K.R.K., Joshi, N.N., (1996) Tetrahedron: Asymmetry, 7, pp. 3147-3152 Santhi, V., Rao, J.M., (2000) Tetrahedron: Asymmetry, 11, pp. 3553-3560 Xu, J., Wei, T., Zhang, Q., (2003) J. Org. Chem., 68, pp. 10146-10151 notenoteTrost, B.M., Fraisse, P.L., Ball, Z.T., (2002) Angew. Chem., Int. Ed., 41, pp. 1059-1061 Ali, I.S., Sudalai, A., (2002) Tetrahedron Lett., 43, pp. 5435-5436 Devine, P.N., Heid, R.M., Tschaen, D.M., (1997) Tetrahedron, 53, pp. 6739-6746 Bracher, F., Litz, T., (1996) Bioorg. Med. Chem., 4, pp. 877-880 Gao, Y., Sharpless, K.B., (1988) J. Org. Chem., 53, pp. 4081-4084 Srebnik, M., Ramachandran, P.V., Brown, H.C., (1988) J. Org. Chem., 53, pp. 2916-2920