Skewphos-Ru(II): An efficient catalyst for asymmetric hydrogenation of functionalized ketones

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6603-6606

  Blanc, Delphine ^a   Henry, Jean Christophe ^a   Ratovelomanana Vidal, Virginie ^a   Genêt, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYST; ENANTIOMER; HYDROGENATION;

EID: 0030846119     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01522-0     Document Type: Article

References (21)

1. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Genêt J. P. in Reductions in Organic Synthesis in A.C.S. symposium series 641, 1996, pp 31-51. Genêt, J. P. Acros Chim. Acta 1995, 1, 4-9. Noyori, R. Asymmetric Catalysis Synthesis, J. Wiley, N. Y. 1994. Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric Synthesis , I. Ojima, N.Y. 1993. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
2. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Genêt J. P. in Reductions in Organic Synthesis in A.C.S. symposium series 641, 1996, pp 31-51. Genêt, J. P. Acros Chim. Acta 1995, 1, 4-9. Noyori, R. Asymmetric Catalysis Synthesis, J. Wiley, N. Y. 1994. Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric Synthesis , I. Ojima, N.Y. 1993. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
3. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Genêt J. P. in Reductions in Organic Synthesis in A.C.S. symposium series 641, 1996, pp 31-51. Genêt, J. P. Acros Chim. Acta 1995, 1, 4-9. Noyori, R. Asymmetric Catalysis Synthesis, J. Wiley, N. Y. 1994. Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric Synthesis , I. Ojima, N.Y. 1993. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
4. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Genêt J. P. in Reductions in Organic Synthesis in A.C.S. symposium series 641, 1996, pp 31-51. Genêt, J. P. Acros Chim. Acta 1995, 1, 4-9. Noyori, R. Asymmetric Catalysis Synthesis, J. Wiley, N. Y. 1994. Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric Synthesis , I. Ojima, N.Y. 1993. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
5. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Genêt J. P. in Reductions in Organic Synthesis in A.C.S. symposium series 641, 1996, pp 31-51. Genêt, J. P. Acros Chim. Acta 1995, 1, 4-9. Noyori, R. Asymmetric Catalysis Synthesis, J. Wiley, N. Y. 1994. Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric Synthesis , I. Ojima, N.Y. 1993. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
6. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Genêt J. P. in Reductions in Organic Synthesis in A.C.S. symposium series 641, 1996, pp 31-51. Genêt, J. P. Acros Chim. Acta 1995, 1, 4-9. Noyori, R. Asymmetric Catalysis Synthesis, J. Wiley, N. Y. 1994. Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric Synthesis , I. Ojima, N.Y. 1993. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
7. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R.; J. Am. Chem. Soc. 1980, 102, 7932-7934. Schmid R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure and Appl. Chem, 1996, 68, 131-138. Schmid, R.; Foricher, J. Cereghetti, M.; Schönholzer, Helv. Chim. Acta 1991, 74, 370-388. Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, H.-J. Hansen, Helv. Chim. Acta 1988, 71, 897-929.
8. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R.; J. Am. Chem. Soc. 1980, 102, 7932-7934. Schmid R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure and Appl. Chem, 1996, 68, 131-138. Schmid, R.; Foricher, J. Cereghetti, M.; Schönholzer, Helv. Chim. Acta 1991, 74, 370-388. Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, H.-J. Hansen, Helv. Chim. Acta 1988, 71, 897-929.
9. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R.; J. Am. Chem. Soc. 1980, 102, 7932-7934. Schmid R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure and Appl. Chem, 1996, 68, 131-138. Schmid, R.; Foricher, J. Cereghetti, M.; Schönholzer, Helv. Chim. Acta 1991, 74, 370-388. Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, H.-J. Hansen, Helv. Chim. Acta 1988, 71, 897-929.
10. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R.; J. Am. Chem. Soc. 1980, 102, 7932-7934. Schmid R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure and Appl. Chem, 1996, 68, 131-138. Schmid, R.; Foricher, J. Cereghetti, M.; Schönholzer, Helv. Chim. Acta 1991, 74, 370-388. Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, H.-J. Hansen, Helv. Chim. Acta 1988, 71, 897-929.
11. a) Genêt, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S; Pfister, X.; Caño de Andrade, M. C.; Laffitte, J.A. Tetrahedron:Asymmetry 1994, 5, 665-674.
12. b) Genêt, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V. ; Mallart, S.; Pfister, X.; Bischoff, L.; Caño de Andrade, M.C.; Darses, S.; Galopin, C.; Laffitte, J.A. Tetrahedron : Asymmetry 1994, 5, 675-690.
13. d) Tranchier, J.-P., Ratovelomanana-Vidal, V., Genet, J.-P.; Tong, S.; Cohen, T. Tetrahedron Lett. 1997, 38, 2951-2954.
14. a) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S.; J. Am. Chem. Soc. 1995, 117, 4423-4424.
15. b) Burk, M. J., Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10131.
16. Both enantiomers of Skewphos (also named BDPP : 2,4-bis(diphenylphosphino)pentane) are commercially avalaible. For some syntheses of SKEWPHOS, see a) MacNeil, P. A.; Roberts, N. K.; Bosnish, B. J. Am. Chem. Soc. 1981, 103, 2273-2280.
17. b) Bakos, J.; Toth, I.; Heil, B.; Marko, L. J. Organomet. Chem, 1985, 279, 23-29.
18. c) Brunner, H.; Terfort, A. Tetrahedron : Asymmetry 1995, 6, 919-922.
19. Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett. 1992, 169-178.
20. According to Bosnich's group, by comparison with rhodium chemistry and catalytic hydrogenation of dehydroaminoacids, the Ru-catalyst may adopt a six membered chelate system for which the chelate ring is stabilized in a chiral skew conformation (b) with both methyl groups in a preferred equatorial disposition rather than the two chair conformation (a) and (c) having one destabilizing axially disposed methyl group and the phenyl groups which are not disposed in a chiral array in respect to ruthenium center. (equation presented)
21. The sense of the enantioselectivity obtained using (S,S)-Skewphos for asymmetric hydrogenation of phenyl thiosulfides could be explained by the preferred transition state where interactions between the phenyl group of the Skewphos and the alkyl chain of the keto group are minimized. (equation presented)