802
U. Matteoli et al. / Tetrahedron: Asymmetry 18 (2007) 797–802
11. Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akuta-
gawa, S.; Inoue, S.; Kasahara, I.; Noyori, R. J. Am. Chem.
Soc. 1987, 109, 1596.
12. (a) Dakoji, S.; Li, D.; Agnihotri, G.; Zhou, H.; Liu, H. J. Am.
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5.4.2. (R)- or (S)-3-Methyl-5-phenyl-pentanenitrile. Com-
pound (R)- or (S)-9, was obtained by treatment of (R)- or
(S)-8 with NH2OHÆHCl in the presence of a catalytic
amount of NaI according to the method developed by Bal-
1
lini et al.21 (90% yield). The GC–MS and H NMR data27
of (R)- or (S)-9 were identical to those reported in the liter-
ature. 13C NMR (CDCl3): d 19.3, 24.5, 29.9, 33.0, 37.5,
118.7, 126.0, 128.2, 128.5, 141.3. Chiral GC conditions:
Chiraldex GT-A column, T = 120 ꢂC (isotherm), nitrogen
14. Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.;
Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473.
flow = 3.5 mL/min, tR = 63.79 min (S), tR = 64.96 min
25
´
`
15. Martın, R.; Islas, G.; Moyano, A.; Pericas, M. A.; Riera, A.
(R). ½aꢁD ¼ þ2:4 (c 2.2, EtOH); (S)-(+)-3-methyl-5-phen-
25
Tetrahedron 2001, 57, 6367.
yl-pentanenitrile; ½aꢁD ¼ ꢀ2:3 (c 2.2, EtOH); (R)-(ꢀ)-3-
16. (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int.
Ed. 1998, 37, 2897; (b) McIntyre, S.; Ho¨rmann, E.; Menges,
F.; Smidt, S. P.; Pfaltz, A. Adv. Synth. Catal. 2005, 347, 282;
(c) Hedberg, C.; Ka¨llstro¨m, K.; Brandt, P.; Hansen, L. K.;
Andersson, P. G. J. Am. Chem. Soc. 2006, 128, 2995; (d)
Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Ho¨rmann, E.;
McIntyre, S.; Menges, F.; Scho¨nleber, M.; Smidt, S. P.;
methyl-5-phenyl-pentanenitrile.
Acknowledgements
Rhodia UK Ltd—Phosphorus Specialties and Derivatives
is acknowledged for generously supplying the BINAP
ligands. Dr. P. Kraft, Mr. A. Alchenberger, Mr. A. Vink-
snaitis and Mr. K. Grman from Givaudan AG are kindly
acknowledged for all the olfactory evaluations. The work
has been performed with the Financial Support of the
MIUR (COFIN 2004).
Wustenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003,
¨
345, 33; (e) Ka¨llstro¨m, K.; Andersson, P. G. Tetrahedron
Lett. 2006, 47, 7477; (f) Bell, S.; Wustenberg, B.; Kaiser, S.;
¨
Menges, F.; Netscher, T.; Pfaltz, A. Science 2006, 311, 642;
(g) Fan, Y.; Cui, X.; Burgess, K.; Hall, M. B. J. Am. Chem.
Soc. 2004, 126, 16688; (h) Perry, M. C.; Cui, X.; Powell, M.
T.; Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Am. Chem.
Soc. 2003, 125, 113.
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