1164
LETTERS
SYNLETT
adequate chlorophosphine (2.5 equivalents) in 5 ml of deoxygenated
diethyl ether was added via a cannula to the aminoalcohol (2 mmol)
dissolved in a mixture of deoxygenated diethyl ether/ triethylamine
(5ml/5ml). The reaction mixture was stirred at room temperature for 20
(4) Agbossou, F.; Carpentier, J.-F.; Hapiot, F.; Suisse, I.; Mortreux, A.
Coord. Chem. Rev. in press.
(5) (a) Agbossou, F.; Carpentier, J.-F.; Hatat, C.; Kokel, N.; Mortreux,
A.; Betz, P.; Goddard, R.; Krüger, C. Organometallics 1995, 14,
2480. (b) Roucoux, A.; Thieffry, L.; Carpentier, J.-F.; Devocelle,
M.; Méliet, C.; Agbossou, F.; Mortreux, A. Organometallics 1996,
15, 2440. (c) Pasquier, C.; Naili, S.; Pelinski, L.; Brocard, J.;
Mortreux, A.; Agbossou, F. Tetrahedron: Asymmetry 1998, 9, 193.
(d) Devocelle, M.; Agbossou, F.; Mortreux, A. Synlett 1997, 1306.
hours while a white solid precipitated (NEt ·HCl). The completion of
3
31
1
the reaction was checked by P{ H}NMR spectroscopy. Then, the
excess of chlorophosphine, ammonium chlorhydrate, and phosphorus
impurities were removed by filtration through basic alumina (1 x 5 cm)
(washed with 2 x 5 ml of diethyl ether). The solvents were removed
from the filtrate under reduced pressure to afford the AMPP ligand
which was further dried under vacuum.
(6) The opposite observation has been related in the case of the
enantioselective hydrogenation of dehydroamino acid derivatives.
See Döbler, C.; Schmidt, U.; Krause, H. W., Kreuzfeld, H.-J.;
Michalik. M. Tetrahedron: Asymmetry 1995, 6, 385.
Acknowledgements. We gratefully thank Lydie Pelinski and Jacques
Muzart for helpful discussions, Nina Hermanns for her help in the
determination of the optical purity of the ligands and Catherine Méliet
for her skilful assistance in obtaining NMR spectra. We thank the
"Centre National de la Recherche Scientifique", the "Ministère de
l'Enseignement Supérieur et de la Recherche" and the "Hermann-
Schlosser-Stiftung" for their financial support. Also we thank the
companies Hoechst AG and Degussa AG for their generous gifts of
chemicals.
(7) (a) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J.
Tetrahedron: Asymmetry 1997, 8, 2761. (b) Stingl, K.; Martens, J.
Liebigs. Ann. Chem. 1994, 491. (c) Wallbaum, S.; Martens, J.
Tetrahedron: Asymmetry 1993, 4, 637. (d) Behnen, W.; Mehler, T.;
Martens, J. Tetrahedron: Asymmetry 1993, 4, 1413.
(8) (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3,
1475. (b) Reiners, I.; Martens, J. Tetrahedron: Asymmetry 1997, 8,
277. (c) Dauelsberg, Ch.; Martens, J. Synth. Commun 1993, 23,
2091.
References and Notes
(9) Reiners, I.; Wilken J.; Martens, J. Tetrahedron: Asymmetry 1995,
6, 3063.
(1) (a) Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric
Synthesis; Ojima, I., Ed.; VCH Publishers, Inc. 1993, Chapter 1, p
1. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis;
Noyori, R., Wiley, New York, 1994, Chapter 2, p 16. (c) Mashima,
K.; Kusano, K.-h.; Sato, N.; Matsumura, Y.-i.; Nozaki, K.;
Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.;
Takaya, H. J. Org. Chem. 1994, 59, 3064. (d) Brunner, H.;
Zettlmeier, W. Handbook of Enantioselective Catalysis with
Transition Metal Compounds, Vol I and II, VCH: Weinheim,
1993.
(10) Behnen, W.; Martens, J. unpublished results.
(11) Farge, D.; Jossin, A.; Ponsinet, G.; Reisdorf, D. German Pat. 2
635 516, 1977; Chem. Abstr. 1977, 87, 5949.
31
1
(12)
P{ H} NMR data at 121 MHz (ppm, CDCl ): (S)-1: 107.5 (s,
3
OPPh ), 45.7 (s, NPPh ); (S)-2: 115.4 (s, OPPh ), 46.7 (s,
2
2
2
NPPh ); (R)-3: 114.2 (s, OPPh ), 61.4 (s, NPPh ); (S)-4: 113.4 (s,
2
2
2
OPCp ), 72.9 (s, NPCp ); (S)-5: 144.0 (s, OPCp ), 56.6 (s,
2
2
2
NPCp ); (R)-6: 143.5 (s, OPCp ), 78.0 (s, NPCp ); (R)-7: 146.7
2
2
2
(s, OPCy ), 77.2 (s, NPCy ).
2
2
(2) (a) Kagan, H. B. In Asymmetric Synthesis, J. D. Morrison, Ed.,
Academic Press, New York, 1985, vol.5, p. 1. (b) Brunner, H. In
Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley:
New York, 1988, p. 129.
(13) The ruthenium precatalysts were prepared in situ by reaction of
one equivalent of Ru(COD)(2-methylallyl) with one equivalent
2
of the adequate AMPP in CH Cl for 20 minutes.
2
2
(14) Seebach, D.; Vettiger, T.; Müller, H.-M.; Plattner, D.; Petter, W.
(3) (a) Holz, J. Quirmbach, M.; Börner, A. Synthesis 1997, 983. (b)
Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.;
Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc.
1998, 120, 1635. (c) Burk, M. J.; Gross, M. F.; Harper, T. G. P.;
Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure & Appl. Chem.
1996, 68, 37. (d) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am.
Chem. Soc. 1997, 119, 1799. (e) Robin, F.; Mercier, F.; Ricard, L.;
Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365.
Liebigs. Ann. Chem. 1990, 687.
(15) Martin, J. W. L.; Palmer, J. A. L.; Wild, S. B. Inorg. Chem. 1984,
23, 2664.
(16) Hapiot, F.; Agbossou, F.; Méliet, C.; Mortreux, A.; Rosair, G. M.;
Welch, A. J. New J. Chem. 1997, 21, 1161.
(17) Carpentier, J.-F.; Mortreux, A. Tetrahedron: Asymmetry 1997, 8,
1083.