The ruthenium BINAP complex, [Ru(OAc)2{(S)-BINAP}], can catalyse the hydrogenation of 2-nitro-1-phenyl-1-propene (1) to give optically active 2-nitro-1-phenylpropane (2) in moderate enantiomeric excess.
(a) NoyoriR., Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons: New York, 1994; (b) R. Noyori and M. Kitamura, In Modern Synthetic Methods; Scheffold, R., ed.; Springer-Verlag: Berlin, 1989; Vol. 5, p.115; (c) Siegel, S. Encyclopedia of Reagents for Organic Synthesis; L. A. Paquette, ed.; John Wiley & Sons; Chichester, 1996; Vol. 6, p 4410; (d) M. A. Bennett and T. W. Matheson. In Comprehensive Organo-metallic Chemistry; G. Wilkinson, F. G. A. Stone, E. W. Abel, eds.; Pergamon Press: Oxford, 1982; Vol. 4, p.931; (e) B. R. James, Homogeneous Hydrogenation; Wiley: New York, 1973; (f) M. Freifelder, Practical Catalytic Hydrogenation; Wiley-Interscience: New York, 1971.
4.
(a) OhtaT., TakayaH., and NoyoriR., Inorg. Chem., 1988, 27, 566. (b) R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, T. Ohta and H. Takaya, J. Am. Chem. Soc. 1986, 108, 7117. (b) T. Ohta, H. Takaya, M. Kitamura, K. Nagai and R. Noyori J. Org. Chem. 1987, 57, 3174.
5.
LiY.J., and IzumiT., J. Chin. Chem. Soc.2002, 49, 505.
6.
MeahY., and MasseyV., Proc. Nat. Acad. Sci.2000, 97, 10733.
7.
The preparation of starting material 1-phenyl-2-nitropropene-1 (1): A solution of benzaldehyde 6.4 g and ammonium acetate 1.0 g in nitroethane 20 ml was heated to reflux for 5 h. On cooling, after removal of the solvent, the residue was purified by column chromatography on silica gel 60 N (neutral; hexane-chloroform, 2: 1, v/v), then recrystallised by hexane and gave 1 as a light yellow crystal 6.2 g (63 %), m.p. 71–73 °C. 1H NMR (CDCl3, 500 MHz) δ 2.46 (s, 3H, CH3), 7.43 (m, 5H, C6H5), 8.10 (s, 1H, CH).
