The application of monodentate secondary phosphine oxide ligands in rhodium- and iridium-catalyzed asymmetric hydrogenation

Tetrahedron Asymmetry

Volumn 15, Issue 14, 2004, Pages 2223-2229

  Jiang, Xiao Bin ^a   Van Den Berg, M ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a   De Vries, Johannes G ^a,b  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZENE DERIVATIVE; CARBAMIC ACID; ESTER DERIVATIVE; IRIDIUM; LIGAND; PHOSPHINE OXIDE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 3843051570     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.05.002     Document Type: Article

References (61)

1. Blaser H.-U., Spindler F., Studer M. Appl. Catal. A: Gen. 221:2001;119
2. Lennon I.C., Moran P.H. Curr. Opin. Drug Disc. Dev. 6:2003;855
3. Feringa B.L. Acc. Chem. Res. 33:2000;346
4. van den Berg M., Minnaard A.J., Schudde E.P., van Esch J., de Vries A.H.M., de Vries J.G., Feringa B.L. J. Am. Chem. Soc. 122:2000;11539
5. (b) van den Berg, M.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. (DSM N. V.), WO 02/04466, 2002
6. Claver C., Fernandez E., Gillon A., Heslop K., Hyett D.J., Martorell A., Orpen A.G., Pringle P.G. Chem. Commun. 2000;961
7. Reetz M.T., Mehler G. Angew. Chem., Int. Ed. 39:2000;3889
8. Guillen F., Fiaud J.-C. Tetrahedron Lett. 40:1999;293
9. Junge K., Oehme G., Monsees A., Riermeier T., Dingerdissen U., Beller M. Tetrahedron Lett. 43:2002;4977
10. van den Berg M., Minnaard A.J., Haak R.M., Leeman M., Schudde E.P., Meetsma A., Feringa B.L., de Vries A.H.M., Maljaars C.E.P., Willans C.E., Hyett D., Boogers J.A.F., Henderickx H.J.W., de Vries J.G. Adv. Synth. Catal. 345:2003;308
11. Peña D., Minnaard A.J., de Vries J.G., Feringa B.L. J. Am. Chem. Soc. 124:2002;14552
12. Zeng Q., Liu H., Mi A., Jiang Y., Li X., Choi M.C.K., Chan A.S.C. Tetrahedron. 58:2002;8799
13. van den Berg M., Haak R.M., Minnaard A.J., de Vries A.H.M., de Vries J.G., Feringa B.L. Adv. Synth. Catal. 344:2002;1003
14. Jia X., Guo R., Li X., Yao X., Chan A.S.C. Tetrahedron Lett. 43:2002;5541
15. Jiang X.-b., Minnaard A.J., Hessen B., Feringa B.L., Duchateau A.L.L., Andrien J.G.O., Boogers J.A.F., de Vries J.G. Org. Lett. 5:2003;1503
16. Dai W.M., Yeung K.K.Y., Leung W.H., Haynes R.K. Tetrahedron: Asymmetry. 14:2003;2821
17. Jandeleit B., Schaefer D.J., Powers T.S., Turner H.W., Weinberg W.H. Angew Chem., Int. Ed. 38:1999;2494
18. Dahmen S., Bräse S. Synthesis. 2001;1431
19. Hoveyda A. Nicolaou K.C., Hanko R., Hartwig W. Handbook of Combinatorial Chemistry. Vol. 2:2002;991-1016 Wiley-VCH, Weinheim
20. de Vries J.G., de Vries A.H.M. Eur. J. Org. Chem. 5:2003;799
21. Haynes R.K., Au-Yeung T.L., Chan W.K., Lam W.L., Li Z.Y., Yeung L.L., Chan A.S.C., Li P., Koen M., Mitchell C.R., Vonwiller S.C. Eur. J. Org. Chem. 2000;3205
22. Haynes R.K., Lam W.W., Yeung L.L. Tetrahedron Lett. 37:1996;4729
23. Haynes R.K., Lam W.W., Williams I.D., Yeung L.L. Chem. Eur. J. 3:1997;2052
24. Kawashima T., Iwanga H., Okazaki R. Chem. Lett. 1993;1531
25. Kawashima T., Iwanga H., Okazaki R. Heteroatom Chem. 6:1995;235
26. Van Leeuwen P.W.N.M., Roobeek C.F. Homogeneous Transition Metal Catalyzed Reactions. Advances in Chemistry Series 230. 1992;367 American Chemical Society, Washington, DC
27. Ghaffar T., Parkins A.W. Tetrahedron Lett. 36:1995;8657
28. Jiang X.-b., Minnaard A.J., Feringa B.L., de Vries J.G. J. Org. Chem. 69:2004;2327
29. Cobley C.J., van den Heuvel M., Abbadi A., de Vries J.G. Tetrahedron Lett. 41:2000;2467
30. Li G.Y., Zheng G., Noonan A.F. J. Org. Chem. 66:2001;8677
31. Li G.Y., Fagan P.J., Watson P.L. Angew. Chem., Int. Ed. 40:2001;1513
32. (c) Li, G. Y. (Du Pont de Nemours and Company, USA). U.S. Patent 6,124,462, 2000
33. (d) Li, G. Y. (Du Pont de Nemours and Company, USA). U.S. Patent 6,291,722 B1, 2001
34. The absolute configuration of 1 is known, see Ref. 13a. The absolute configuration of 2-7 was tentatively assigned according to the order of elution of their enantiomers on chiral HPLC compared to 1
35. Brown J.M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. 1:1999;Springer, Berlin. Chapter 5.1
36. (a) Ref. [8b]
37. Holz J., Monsees A., Jiao H.J., You J.S., Komarov I.V., Fischer C., Drauz K., Börner A. J. Org. Chem. 68:2003;1701. and references cited therein
38. Tang W.J., Wu S.L., Zhang X.M. J. Am. Chem. Soc. 125:2003;9570
39. See Section 4
40. Ref. [8a]
41. Burk M.J., Bienewald F. Beller M., Bolm C. Transition Metals for Organic Synthesis. Vol. 2:1998;20 Wiley-VCH, Weinheim
42. Yamanoi Y., Imamoto T. J. Org. Chem. 64:1999;2988
43. Miura T., Imamoto T. Tetrahedron Lett. 40:1999;4833
44. Kuwano R., Sawamura M., Ito Y. Bull. Chem. Soc. Jpn. 73:2000;2571
45. Gridnev I.D., Yamanoi Y., Higashi N., Tsuruta H., Yasytake M., Imamoto T. Adv. Synth. Catal. 343:2001;118
46. Burk M.J., Gross M.F., Martinez J.P. J. Am. Chem. Soc. 117:1995;9375
47. Schmidt U., Lieberknecht A., Wild J. Synthesis. 1988;159
48. Schmidt U., Griesser H., Leitenberger V., Lieberknecht A., Mangold R., Meyer R., Riedl B. Synthesis. 1992;487
49. Lightfoot A., Schnider P., Pfaltz A. Angew. Chem., Int. Ed. 37:1998;2897
50. Pfaltz A., Blankenstein J., Hilgraf R., Hormann E., McIntyre S., Menges F., Schonleber M., Smidt S.P., Wustenberg B., Zimmermann N. Adv. Synth. Catal. 345:2003;33
51. Cui X.H., Burgess K. J. Am. Chem. Soc. 125:2003;14212
52. Liu D., Tang W.J., Zhang X.M. Org. Lett. 6:2004;513
53. Burk M.J. Acc. Chem. Res. 33:2000;363
54. Tang W.J., Liu D., Zhang X.M. Org. Lett. 5:2003;205
55. Reetz M.T., Goossen L.J., Meiswinkel A., Paetzold J., Jensen J.F. Org. Lett. 5:2003;3099
56. Ref. 19
57. Ref. 24
58. Marcovici-Mizrahi D., Gottlieb H.E., Marks V., Nudelman A. J. Org. Chem. 61:1996;8402
59. Supplied by Argonaut Technologies
60. Treating DMSO with sodium hydride should be done with caution. Explosive mixtures can form. A mixture of sodium hydride (4.5 mol) and dimethyl sulfoxide (18.4 mol) may explode after about 1 h. Vogel A.I. Furniss B.S., Hannaford A.J., Smith P.W.G., Tatchell A.R. Vogel's Textbook of Practical Organic Chemistry. 5th ed.:1989;412 Longman, London
61. During the formation of dimsyl anion from NaH and DMSO the temperature should not exceed 70°C. Above this temperature extensive decomposition of the anion occurs. This decomposition also occurs when longer reaction times are required. Corey E.J., Chaykovsky M. J. Am. Chem. Soc. 87:1965;1345