Novel rhodium catalyst for asymmetric hydroformylation of styrene: Study of electronic and steric effects of phosphorus seven-membered ring ligands

Journal of Molecular Catalysis A: Chemical

Volumn 280, Issue 1-2, 2008, Pages 148-155

  Erre, Giulia ^a   Enthaler, Stephan ^a   Junge, Kathrin ^a   Gladiali, Serafino ^b   Beller, Matthias ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

Asymmetric hydroformylation; Monodentate phosphines; Rhodium

Indexed keywords

COMPLEXATION; HYDROFORMYLATION; LIGANDS; PHOSPHORUS; RHODIUM;

ASYMMETRIC HYDROFORMYLATION; BIDENTATE LIGANDS; MONODENTATE PHOSPHINES;

STYRENE;

EID: 38349057536     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2007.10.023     Document Type: Article

References (54)

1. van Leeuwen P.W.N.M., and Claver C. Rhodium Catalyzed Hydroformylation (2000), Kluwer Academic Publishers, Dordrecht, Netherlands
2. Diéguez M., Pàmies O., and Claver C. Tetrahedron: Asymmetry 15 (2004) 2113-2122
3. Gladiali S., Bayón J.C., and Claver C. Tetrahedron: Asymmetry 6 (1995) 1453-1474
4. Agbossou F., Carpentier J.-F., and Montreux A. Chem. Rev. 95 (1995) 2485-2506
5. In: Nozaki K., Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis (1999), Springer, Heidelberg 381-413
6. Beller M., and Kumar K. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis vol. I (2004), Wiley-VCH Verlag, Weinheim 29-55
7. Botteghi C., Paganelli S., Schionato A., and Marchetti M. Chirality (1991) 355-369
8. J.E. Babin, G.T. Whiteker, WO 9303839, 1993.
9. Whiteker G.T., Briggs J.R., Babin J.E., and Barner B.A. Chemical Industries vol. 89 (2003), Marcel Dekker, New York pp. 359-367
10. Cobley C.J., Gardner K., Klosin J., Praquin C., Hill C., Whiteker G.T., Zanotti-Gerosa A., Petersen J.L., and Abboud K.A. J. Org. Chem. 69 (2004) 4031-4040
11. Cobley C.J., Klosin J., Qin C., and Whiteker G.T. Org. Lett. 6 (2004) 3277-3280
12. Sakai N., Mano S., Nozaki K., and Takaya H. J. Am. Chem. Soc. 115 (1993) 7033-7034
13. Nozaki K., Sakai N., Nanno T., Higashijima T., Mano S., Horiuchi T., and Takaya H. J. Am. Chem. Soc. 119 (1997) 4413-4423
14. Horiuchi T., Shirakawa E., Nozaki K., and Takaya H. Organometallics 16 (1997) 2981-2986
15. Axtell A.T., Klosin J., and Abboud K.A. Organometallics 25 (2006) 5003-5009
16. Axtell A.T., Cobley C.J., Klosin J., Whiteker G.T., Zanotti-Gerosa A., and Abboud K.A. Angew. Chem. Int. Ed. 44 (2005) 5834-5838
17. Yan Y., and Zhang X. J. Am. Chem. Soc. 128 (2006) 7198-7202
18. Breeden S., Cole-Hamilton D.J., Foster D.F., Schwarz G.J., and Wills M. Angew. Chem. Int. Ed. 39 (2000) 4106
19. Clark T.P., Landis C.R., Freed S.L., Klosin J., and Abboud K.A. J. Am. Chem. Soc. 127 (2005) 5040-5042
20. Junge K., Oehme G., Monsees A., Riermeier T., Dingerdissen U., and Beller M. J. Organomet. Chem. 675 (2003) 91-96
21. Junge K., Oehme G., Monsees A., Riermeier T., Dingerdissen U., and Beller M. Tetrahedron Lett. 43 (2002) 4977-4980
22. Junge K., Hagemann B., Enthaler S., Spannenberg A., Michalik M., Oehme G., Monsees A., Riermeier T., and Beller M. Tetrahedron: Asymmetry 15 (2004) 2621-2631
23. Junge K., Hagemann B., Enthaler S., Oehme G., Michalik M., Monsees A., Riermeier T., Dingerdissen U., and Beller M. Angew. Chem. 116 (2004) 5176-5179
24. Junge K., Hagemann B., Enthaler S., Oehme G., Michalik M., Monsees A., Riermeier T., Dingerdissen U., and Beller M. Angew. Chem. Int. Ed. 43 (2004) 5066-5069
25. Hagemann B., Junge K., Enthaler S., Michalik M., Riermeier T., Monsees A., and Beller M. Adv. Synth. Catal. 347 (2005) 1978-1986
26. Junge K., Hagemann B., Enthaler S., Erre G., and Beller M. ARKIVOC 5 (2007) 50-66
27. Gladiali S., Dore A., Fabbri D., De Lucchi O., and Manassero M. Tetrahedron: Asymmetry (1994) 511-514
28. First synthesis of this ligand was reported by:. Kasák P., Mereiter K., and Widhalm M. Tetrahedron: Asymmetry 16 (2005) 3416-3426
29. For an alternative synthesis see:. Enthaler S., Erre G., Junge K., Michalik D., Spannenberg A., Marras F., Gladiali S., and Beller M. Tetrahedron: Asymmetry 18 (2007) 1288-1298
30. Allen D.A., and Taylor B.F. J. Chem. Soc. Dalton (1982) 51-54
31. Holz J., Zayas O., Jiao H., Baumann W., Spannenberg A., Monsees A., Riermeier T.H., Almena J., Kadyrov R., and Börner A. Chem. Eur. J. 12 (2006) 5001-5013
32. 4 and 2.1 mol% 4j the α-amino acid derivatives were hydrogenated in excellent yields (methyl 2-acetamidocinnamate: 98%; methyl 2-acetamidoacrylate: >99%) and good enantioselectivities (methyl 2-acetyl phenylalanine: 87% ee; methyl 2-acetyl alanine: 71% ee) [reaction time: 24 h; hydrogen pressure: 1.3 bar; 25 °C; solvent: toluene]. Furthermore, the same catalyst was active in the hydrogenation of β-amino acid precursors. Here, (Z)-methyl 3-acetamidobut-2-enoate was hydrogenated with good enantioselectivity (64% ee (S), conversion: 53%; reaction time: 24 h; hydrogen pressure: 50 bar; 10 °C; 24 h; solvent: ethanol), while the hydrogenation of the corresponding E-isomer was poorly enantioselective (4% ee (S), conversion: 82%; reaction time: 24 h; hydrogen pressure: 2.5 bar; 10 °C; 24 h; solvent: 2-propanol).
33. Reetz M.T., Sell T., Meiswinkel A., and Mehler G. Angew. Chem. Int. Ed. 42 (2003) 790-793
34. Reetz M.T., and Mehler G. Tetrahedron Lett. 44 (2003) 4593-4596
35. Reetz M.T., Mehler G., and Meiswinkel A. Tetrahedron: Asymmetry 15 (2004) 2165-2167
36. Reetz M.T., and Li X. Angew. Chem. Int. Ed. 44 (2005) 2959-2962
37. Duursma A., Hoen R., Schuppan J., Hulst R., Minnaard A.J., and Feringa B.L. Org. Lett. 5 (2003) 3111-3113
38. Duursma A., Peña D., Minnaard A.J., and Feringa B.L. Tetrahedron: Asymmetry 16 (2005) 1901-1904
39. Peña D., Minnaard A.J., Boogers J.A.F., de Vries A.H.M., and Feringa B.L. Org. Biomol. Chem. 1 (2003) 1087-1089
40. Reetz M., and Li X. Angew. Chem. Int. Ed. 44 (2005) 2962-2964
41. ® A: for selective catalytic applications see:
42. Ehrentraut A., Zapf A., and Beller M. Synlett (2000) 1589-1592
43. Zapf A., Ehrentraut A., and Beller M. Angew. Chem. Int. Ed. 39 (2000) 4153-4155
44. Tewari A., Hein M., Zapf A., and Beller M. Tetrahedron 61 (2005) 9705-9709
45. Ehrentraut A., Zapf A., and Beller M. J. Mol. Catal. 182/183 (2002) 515-523
46. Ehrentraut A., Zapf A., and Beller M. Adv. Synth. Catal. 344 (2002) 209-217
47. Klaus S., Neumann H., Zapf A., Strübing D., Hübner S., Almena J., Riermeier T., Groß P., Sarich M., Krahnert W.-R., Rossen K., and Beller M. Angew. Chem. Int. Ed. 45 (2006) 154-158
48. Neumann H., Brennführer A., Groß P., Riermeier T., Almena J., and Beller M. Adv. Synth. Catal. 348 (2006) 1255-1261
49. Kurz L., Lee G., Morgans D., Waldyke M.J., and Ward T. Tetrahedron Lett. 31 (1990) 6321-6324
50. Uozumi Y., Tanahashi A., Lee S.-Y., and Hayashi T. J. Org. Chem. 58 (1993) 1945-1948
51. Yan M., Yang L.-W., Wong K.-Y., and Chan A.S.C. Chem. Commun. (1999) 11
52. Yan M., Zhou Z.-Y., and Chan A.S.C. Chem. Commun. (2000) 115
53. Su L., Li X., Chan W.L., Jia X., and Chan A.S.C. Tetrahedron: Asymmetry 14 (2003) 1865
54. Baker M.J., and Pringle P.G. Chem. Commun. (1991) 1292