Adaptative biaryl phosphite-oxazole and phosphite-thiazole ligands for asymmetrie Ir-catalyzed hydrogenation of alkenes

Chemistry - A European Journal

Volumn 16, Issue 15, 2010, Pages 4567-4576

  Diéguez, Montserrat ^a   Mazuela, Javier ^a   Paptchikhine, Alexander ^b   Pàmies, Oscar ^a   Andersson, Pher G ^b  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

Alkenes; Asymmetric catalysis; Hydrogenation; Iridium; PN ligands

Indexed keywords

ALKENES; ASYMMETRIC CATALYSIS; ASYMMETRIC HYDROGENATION; CHIRAL INFORMATION; ENANTIOMERIC EXCESS; HETEROCYCLIC RINGS; OXAZOLES; P-N LIGANDS; TERMINAL ALKENES;

CATALYSIS; ENANTIOSELECTIVITY; HYDROGENATION; IRIDIUM; OLEFINS;

LIGANDS;

ALKENE; IRIDIUM; LIGAND; OXAZOLE DERIVATIVE; PHOSPHITE; THIAZOLE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; HYDROGENATION; P,N LIGANDS; STEREOISOMERISM;

ALKENES; ASYMMETRIC CATALYSIS; HYDROGENATION; IRIDIUM; P,N LIGANDS;

ALKENES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROGENATION; IRIDIUM; LIGANDS; MOLECULAR STRUCTURE; OXAZOLES; PHOSPHITES; STEREOISOMERISM; THIAZOLES;

EID: 77950797707     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903350     Document Type: Article

References (66)

1. See for instance: a) Catalytic Asymmetric Synthesis. 2nd ed. (Ed.: I. Ojima), Wiley-VCH, Weinheim. 2000;
2. b) Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed. (Eds. : B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim. 2002;
3. c) Asymmetric Catalysis on Industrial Scale : Challenges, Approaches and Solutions (Eds.: H. U Blaser, E. Schmidt), Wiley-VCH, Weinheim, 2004;
4. d) Comprehensice Asymmetric Catalysis, Vols. 1-3 (Eds.: E.N. Jacobsen. A. Pfaltz, H. Yamamoto), Springer. Berlin. 1999:
5. e) R. Noyori. Asymmetric Catalysis in Organic Synthesis, Wiley, New York. 1994.
6. For recent reviews, see: a) K. Källström, I. Munslow, P. G. Andersson, Chem. Eur. J. 2006, 12, 3194;
7. b) S. J. Roseblade. A. Pfaltz, Acc. Chem. Res. 2007, 40. 1402:
8. c) T. L. Church, P. G. Andersson. Coord. Chem. Rev. 2008, 252, 513;
9. d) X. Cui, K. Burgess, Chem. Rev. 2005. 105. 3272.
10. See. for instance: a) W. Tang. W. Wang, X. Zhang, Angew. Chem. 2003. 115, 973:
11. Angew. Chem. Int. Ed. 2003. 42, 943:
12. b) D.-R. Hou. J. Reibenspies, T. J. Colacot, K. Burgess, Chem. Eur. J. 2001, 7, 5391
13. c) R G. Cozzi, F. Menges. S. Kaiser, Synlett 2003, 0833:
14. d) A. Lightfoot. P. Schnider. A. Pfaltz. Angew. Chem. 1998, 110, 3047:
15. Angew. Chem. Int. Ed. 1998. 37, 2897:
16. e) F. Menges. M. Neuburger. A. Pfaltz, Org. Lett. 2002, 4, 4713:
17. f) D. Liu. W. Tang. X. Zhang, Org. Lett. 2004, 6, 513.
18. See, for instance: a) M. C Perry, X. Cui. M. T. Powell. D.-R. Hou. J. H. Reibenspies, K. Burgess. J. Am. Chem. Soc. 2003, 125, 5391
19. b) J. Blankenstein, A. Pfaltz. Angew. Chem. 2001, 113, 4577:
20. Angew. Chem. Int. Ed. 2001, 40, 4445:
21. c) S. Kaiser, P. S. Smidt. A. Pfaltz, Angew. Chem. 2006, 118. 5318;
22. Angew. Chem. Int. Ed. 2006. 45, 5194;
23. d) K. Källström, C. Hedberg, P. Brandt, P. Bayer. R G. Andersson, J. Am. Chem. Soc. 2004, 126, 14308;
24. e) M. Engman, J. S. Diesen, A. Paptchikhine, P. G. Andersson, J. Am. Chem. Soc. 2007, 129, 4536;
25. f) A. Trifonova, J. S. Diesen, P. G. Andersson, Chem. Eur. J. 2006, 12, 2318:
26. g) F. Menges, A. Pfaltz. Adv. Synth. Catal. 2002, 344, 4044;
27. h) W. J. Drury III. N. Zimmermann. M. Keenan, M. Hayashi. S. Kaiser. R. Goddard. A. Pfaltz. Angew. Chem. 2004. 116, 72:
28. Angew. Chem. Int. Ed. 2004. 43, 70:
29. i) C. Hedberg, K. Källström, P. Brandt, L. K. Hansen, P. G. Andersson. J. Am. Chem. Soc. 2006, 128, 2995.
30. a) M. Diéguez, J. Mazuela, O. Pàmies. J. J. Verendel. P. G. Andersson, J. Am. Chem. Soc. 2008, 130, 7208;
31. b) M. Diéguez. J. Mazuela. O. Pàmies, J. J. Verendel, P. G. Andersson, Chem. Commun. 2008, 3888;
32. c) J. Mazuela, J. J. Verendel, M. Coll, B. Schäffner. A. Börner, P. G. Andersson. O. Pàmies, M. Diéguez, J. Am. Chem. Soc. 2009, 131, 12344.
33. J. Mazuela, A. Paptchikhine. R Tolstoy, O. Pàmies, M. Diéguez, P. G. Andersson, Chem. Eur. J. 2010, 16, 620.
34. The only success in hydrogenating highly unfunctionalized Z-trisubstituted olefins by using ligands 2 and 3 can be found with the lessdemanding 6-methoxy-l-methylene-l,2,3.4-lelrahydronaphlhalene (S6), see references [4d,4i].
35. P. Cheruku, S. Gohil, P. G. Andersson, Org. Lett. 2007, 9, 1659.
36. Unpublished results (i.e., for substrate S13, ee values up to 41%).
37. J. A. Joule, K. Mills, Heterocyclic Chemistry, 4th ed., Blackwell Science. Oxford. 2000.
38. For some representative examples, see: a) "Chiral Diphosphinites. Diphosphoniles, Diphosphiles and Mixed PO-Ligands": C. Claver, O. Pàmies, M. Diéguez in Phosphorous Ligands in Asymmetric Catalysis, Vol.2 (Ed.: A. Borner). Wiley-VCH, Weinheim, 2008, Chapter 3;
39. b) M. Diéguez. O. Pàmies. Acc. Chem. Res. 2010, 43, 312:
40. c) M. Diéguez, A. Ruiz. C. Claver, J. Org. Chem. 2002, 67, 3796:
41. d) M. T. Reetz. G. Mehler, Angew. Chem. 2000, 112, 4047:
42. Angew. Chem. Int. Ed. 2000, 39. 3889;
43. e) M. Yan, Z. Y. Zhou. A. S. C. Chan. Chem. Commun. 2000, 115;
44. f) M. Diéguez, A. Ruiz, C Claver, Tetrahedron: Asymmetry 2001, 12, 2895;
45. g) O. Pàmies. M. Diéguez, C Claver, J. Am. Chem. Soc. 2005, 127. 3646:
46. h) M. Diéguez, O. Pàmies. C. Claver, Chem. Commun. 2005, 1221;
47. i) Y. Mata. O. Pàmies. M. Diéguez, Chem. Eur. J. 2007, 13, 3296.
48. The rapid ring inversions (atropoisomerization) in the biaryl phosphite moiety is usually stopped upon coordination to the metal center. See, for example: a) G. X H. Buisman. van der Veen. L. A.; A. Klootwijk, W. G. X de Lange, P. C. J. Kamer, P. W. N. M. van Leeuwen, D. Vogt. Organometallics 1997, 16, 2929;
49. A. Klootwijk. W. G. J. de Lange. P. C. J. Kamer, R W. N. M. van Leeuwen. D. Vogt, Organometallics 1997, 16, 2929;
50. b) M. Diéguez, O. Pàmies. A. Ruiz, C. Claver, S. Castillón, Chem. Eur. J. 2001, 7, 3086;
51. c) O. Pàmies, M. Diéguez, G. Net, A. Ruiz. C. Claver, J. Org. Chem. 2001, 66, 8364;
52. d) M. Diéguez, O. Pàmies. Chem. Eur. J. 2008, 14, 3653;
53. e) O. Pàmies. M. Diéguez. Chem. Eur. J. 2008, 14, 944.
54. For successful applications of Ir catalysts, see: a) S. McIntyre. E. Hörmann, F. Menges. S. P. Smidt. A. Pfaltz, Adv. Synth. Catal. 2005, 347, 282:
55. b) reference [4b];
56. c) reference [4d]:
57. d) reference [5c].
58. For successful applications of Sm. Ru, and Rh complexes, see: a) V. P. Conticello, L. Brard, M. A. Giardello. Y. Tsuji, M. Sabat C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114. 2761;
59. b) M. A. Giardello, V. P. Conticello, L. Brard. M. R. Gagné, T. J. Marks. J. Am. Chem. Soc. 1994, 116, 10241;
60. c) G. S. Forman, T. Ohkuma. W. P. Hems. R. Noyori. Tetrahedron Lett. 2000, 41, 9471:
61. d) T.T. Co, T. J. Kim, Chem. Commun. 2006, 3537.
62. See. for instance: a) A. Abate. E. Brenna, C. Fuganti, G. G. Gatti. T. Givenzana. L. Malpezzi. S. Serra. J. Org. Chem. 2005, 70, 1281:
63. b) K. Drescher. A. Haupt. L. Unger. S. C. Rutner, W. Braje. R. Grandel, C. Henry, G. Backfisch, A. Beyerbach, W. Bisch, WO Patent 2006/040182Al.
64. See. for instance: a) I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063:
65. b) G. R. Jones, Y. Landais, Tetrahedron 1996. 52. 7599:
66. c) W. Bains. R. Tacke, Curr. Opin. Drug Discovery Dev. 2003, 6, 526.