Asymmetric Hydrogenation of α, β, and γ-Aminoketones Catalyzed by Cationic Rhodium(I){AMPP} Complexes

Synlett

Volumn 1997, Issue 11, 1997, Pages 1306-1308

  Devocelle, Marc ^a   Agbossou, Francine ^a   Mortreux, André ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002278650     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1004     Document Type: Article

References (21)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994; Chapter 2, p 56.
2. (b) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993; Chapter 1.
3. Kitamura, M.; Okuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
4. (a) Hayashi, T.; Katsumura, A.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 425.
5. (b) Hayashi, T; Mise, T.; Kumada, M. ibid. 1976, 4351.
6. (c) Toros, S.; Kollar, L.; Heil, B.; Marko, L. J. Organomet. Chem. 1982, 232, C17.
7. (c) Takahashi, H.; Sakuraba, S.; Takeda, H.; Achiwa, K. J. Am. Chem. Soc. 1990, 112, 5876.
8. (d) Takeda, H.; Hosokawa, S.; Aburatani, M.; Achiwa, K. Synlett 1991, 193.
9. (e) Takeda, H.; Tachinami, T.; Aburatani, M.; Takahashi, H.; Motimoto, T.; Achiwa, K. Tetrahedron Lett. 1989, 30, 363.
10. (f) Sakuraba, S.; Nakajima, N.; Achiwa, K. Tetrahedron : Asymmetry 1993, 4, 1457.
11. (g) Sakuraba, S.; Achiwa, K. Synlett 1991, 689.
12. (h) Sakuraba, S.; Nakajima, N.; Achiwa, K. Synlett 1992, 829.
13. (a) Agbossou, F.; Carpentier, J.-F.; Hatat, C.; Kokel, N.; Mortreux, A.; Betz, P.; Goddard, R.; Krüger, C. Organometallics 1995, 14, 2480.
14. (b) Roucoux, A.; Suisse, I.; Devocelle, M.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A. Tetrahedron: Asymmetry 1996, 7, 379.
15. (c) Roucoux A., Thieffry L., Carpentier J.-F., Devocelle M., Meliet C., Agbossou F., Mortreux A. Organometallics 1996, 15, 2440.
16. Roucoux, A.; Devocelle, M.; Carpentier, J.F.; Agbossou, F.; Mortreux, A. Synlett 1995, 358.
17. 4 is commercially available.
18. Substrates 7, 9 and 11 were commercially available. The synthesis of 8 was adapted from Chapman, N. B.; Clarke, K.; Harvey, D. J. J. Chem. Soc. (C) 1971, 1202. The syntheses of 10 and 12 were adapted from ref 3h.
19. Sullivan, H. R.; Beck, J. R.; Pohland, A. J. Org. Chem. 1963, 28, 2381.
20. Heating a 0.1M solution of 11 in methanol under 50 atm of hydrogen at 50 °C during 22 h leads to 71 % of β-elimination.
21. Devocelle, M.; Agbossou, F.; Mortreux, A. manuscript in preparation.