Asymmetric synthesis of fluorinated β-hydroxy esters via ruthenium-mediated hydrogenation

Journal of Organometallic Chemistry

Volumn 603, Issue 1, 2000, Pages 128-130

  Blanc, D ^a   Ratovelomanana Vidal, V ^a   Gillet, J P ^b   Genet J P ^a  

^a CNRS   (France)

^b ARKEMA   (France)

Author keywords

Chiral hydrogenation; Fluoroorganic compounds; Ruthenium catalysts

Indexed keywords

EID: 0000336229     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00174-1     Document Type: Article

References (29)

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21. For some reviews see: (a) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 30 (1997) 97. (b) J.P. Genêt, Reductions in Organic Synthesis in ACS Symposium Series 641 (1996) 31. (c) J.P. Genêt, in: G.R. Stephenson (Ed.), Advances in Asymmetric Synthesis, Chapman and Hall, London, 1996, p. 60. (d) J.P. Genêt, Acros Chim. Acta 1 (1995) 4. (e) R. Noyori, Asymmetric Catalytic Synthesis, Wiley, New York, 1994. (f) H. Takaya, T. Ohta, R. Noyori, Catalytic Asymmetric Synthesis, I. Ojima, New York, 1993. (g) R. Noyori, H. Takaya, Acc. Chem. Res. 23 (1990) 345.
22. For some reviews see: (a) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 30 (1997) 97. (b) J.P. Genêt, Reductions in Organic Synthesis in ACS Symposium Series 641 (1996) 31. (c) J.P. Genêt, in: G.R. Stephenson (Ed.), Advances in Asymmetric Synthesis, Chapman and Hall, London, 1996, p. 60. (d) J.P. Genêt, Acros Chim. Acta 1 (1995) 4. (e) R. Noyori, Asymmetric Catalytic Synthesis, Wiley, New York, 1994. (f) H. Takaya, T. Ohta, R. Noyori, Catalytic Asymmetric Synthesis, I. Ojima, New York, 1993. (g) R. Noyori, H. Takaya, Acc. Chem. Res. 23 (1990) 345.
23. For some reviews see: (a) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 30 (1997) 97. (b) J.P. Genêt, Reductions in Organic Synthesis in ACS Symposium Series 641 (1996) 31. (c) J.P. Genêt, in: G.R. Stephenson (Ed.), Advances in Asymmetric Synthesis, Chapman and Hall, London, 1996, p. 60. (d) J.P. Genêt, Acros Chim. Acta 1 (1995) 4. (e) R. Noyori, Asymmetric Catalytic Synthesis, Wiley, New York, 1994. (f) H. Takaya, T. Ohta, R. Noyori, Catalytic Asymmetric Synthesis, I. Ojima, New York, 1993. (g) R. Noyori, H. Takaya, Acc. Chem. Res. 23 (1990) 345.
24. For some reviews see: (a) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 30 (1997) 97. (b) J.P. Genêt, Reductions in Organic Synthesis in ACS Symposium Series 641 (1996) 31. (c) J.P. Genêt, in: G.R. Stephenson (Ed.), Advances in Asymmetric Synthesis, Chapman and Hall, London, 1996, p. 60. (d) J.P. Genêt, Acros Chim. Acta 1 (1995) 4. (e) R. Noyori, Asymmetric Catalytic Synthesis, Wiley, New York, 1994. (f) H. Takaya, T. Ohta, R. Noyori, Catalytic Asymmetric Synthesis, I. Ojima, New York, 1993. (g) R. Noyori, H. Takaya, Acc. Chem. Res. 23 (1990) 345.
25. For some reviews see: (a) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 30 (1997) 97. (b) J.P. Genêt, Reductions in Organic Synthesis in ACS Symposium Series 641 (1996) 31. (c) J.P. Genêt, in: G.R. Stephenson (Ed.), Advances in Asymmetric Synthesis, Chapman and Hall, London, 1996, p. 60. (d) J.P. Genêt, Acros Chim. Acta 1 (1995) 4. (e) R. Noyori, Asymmetric Catalytic Synthesis, Wiley, New York, 1994. (f) H. Takaya, T. Ohta, R. Noyori, Catalytic Asymmetric Synthesis, I. Ojima, New York, 1993. (g) R. Noyori, H. Takaya, Acc. Chem. Res. 23 (1990) 345.
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27. (a) M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, R. Noyori, J. Am. Chem. Soc. 110 (1988) 629.
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29. 3) (3.2 mg, 0.01 mmol) were placed in a 10 ml glass tube and 1 ml of anhydrous acetone were added dropwise. A methanolic solution of HBr (122 μl, 0.18 M) was added dropwise to the suspension. The reaction mixture was stirred at room temperature for about 30 min and a resulting yellow suspension was observed. The solvent was removed under vacuum. The yellow solid residue was used as catalyst for the hydrogenation reaction. Methanol or ethanol (2 ml) and appropriate substrate (1 mmol) were added and the reaction vessel were placed then in a 500 ml stainless steel autoclave under argon. The autoclave was then pressurized to the desired hydrogen pressure and the reaction was allowed to proceed until complete conversion.