Highly modular C1-symmetric chiral (P,N) ligands with a stereolabile P center: Experimental and theoretical studies

Chemistry - A European Journal

Volumn 20, Issue 3, 2014, Pages 745-751

  Humbert, Nicolas ^a   Larionov, Evgeny ^a   Mantilli, Luca ^a   Nareddy, Pradeep ^a   Besnard, Céline ^a   Guénée, Laure ^a   Mazet, Clément ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

arylation; asymmetric catalysis; chirality; N,P ligands; stereoinversion

Indexed keywords

ARYLATIONS; ASYMMETRIC CATALYSIS; DISTINCT ELEMENTS; N ,P LIGANDS; STEREO-SELECTIVE; STEREOINVERSION; THEORETICAL STUDY; THERMAL INVERSION;

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; CHIRALITY; PHOSPHORUS;

LIGANDS;

ALDEHYDE; ALLYL ALCOHOL; CARBON; LIGAND; NITROGEN; PHOSPHORUS; PROPANOL;

ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMISTRY; CHIRALITY; CONFORMATION; N,P LIGANDS; STEREOINVERSION; STEREOISOMERISM; THEORETICAL MODEL; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

ARYLATION; ASYMMETRIC CATALYSIS; CHIRALITY; N,P LIGANDS; STEREOINVERSION;

ALDEHYDES; CARBON; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; LIGANDS; MODELS, THEORETICAL; MOLECULAR CONFORMATION; NITROGEN; PHOSPHORUS; PROPANOLS; STEREOISOMERISM; THERMODYNAMICS;

EID: 84892370444     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303146     Document Type: Article

References (67)

1. Comprehensive Asymmetric Catalysis (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999
2. Fundamentals of Asymmetric Catalysis, (Eds.:, P. J. Walsh, M. C. Kozlowski,), University Science Books, Sausalito, 2009.
3. Privileged Chiral Ligands and Catalysts (Ed.:, Q.-L. Zhou,), Wiley-VCH, Weinheim, 2011
4. T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691.
5. M. T. Reetz, Angew. Chem. 2008, 120, 2592
6. Angew. Chem. Int. Ed. 2008, 47, 2556
7. C. A. Müller, C. Markert, A. M. Teichert, A. Pfaltz, Chem. Commun. 2009, 1607
8. J. Meeuwissen, J. N. H. Reek, Nat. Chem. 2010, 2, 615
9. J. Wieland, B. Breit, Nat. Chem. 2010, 2, 832
10. R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603
11. K. Brak, E. N. Jacobsen, Angew. Chem. 2013, 125, 558
12. Angew. Chem. Int. Ed. 2013, 52, 534.
13. P. J. Walsh, A. E. Lurain, J. Balsells, Chem. Rev. 2003, 103, 3297.
14. K. Mikami, S. Matsukawa, Nature 1997, 385, 613
15. S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1997, 8, 815.
16. For reviews, see: a) K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676
17. Angew. Chem. Int. Ed. 2000, 39, 3532
18. K. Mikami, M. Yamanaka, Chem. Rev. 2003, 103, 3369
19. K. Mikami, K. Aikawa, in New Frontiers in Asymmetric Catalysis (Eds.:, K. Mikami, M. Lautens,), Wiley, Hoboken, 2007
20. K. Aikawa, K. Mikami, Chem. Commun. 2012, 48, 11050.
21. For selected studies on the stereodynamics of biaryl tropoisomeric ligands, see: a) O. Desponds, M. Schlosser, Tetrahedron Lett. 1996, 37, 47
22. M. Tudor, J. J. Becker, P. S. White, M. R. Gagné, Organometallics 2000, 19, 4376
23. F. Maier, O. Trapp, Angew. Chem. 2012, 124, 3039
24. Angew. Chem. Int. Ed. 2012, 51, 2985
25. F. Maier, O. Trapp, Chirality 2013, 25, 126; for examples of epimerization of diastereomeric P ligands, see
26. E. Vedejs, Y. Donde, J. Am. Chem. Soc. 1997, 119, 9293
27. E. Vedejs, Y. Donde, J. Org. Chem. 2000, 65, 2337.
28. L. Horner, H. Büthe, H. Siegel, Tetrahedron Lett. 1968, 4023
29. W. S. Knowles, M. J. Sabacky, Chem. Commun. (London) 1968, 1445
30. J. F. Teichert, B. L. Feringa, Angew. Chem. 2010, 122, 2538
31. Angew. Chem. Int. Ed. 2010, 49, 2486; for a review on binepines, see
32. S. Gladiali, E. Alberico, K. Junge, M. Beller, Chem. Soc. Rev. 2011, 40, 3744.
33. P-Stereogenic Ligands in Enantioselective Synthesis (Ed.:, A. Grabulosa,), RSC, Cambridge, 2011
34. K. Michal-Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375
35. D. S. Glueck, Chem. Eur. J. 2008, 14, 7108
36. J. S. Harvey, V. Gouverneur, Chem. Commun. 2010, 46, 7477.
37. P. Nareddy, L. Mantilli, L. Guénée, C. Mazet, Angew. Chem. 2012, 124, 3892
38. Angew. Chem. Int. Ed. 2012, 51, 3826.
39. For a short review, see: a) C. Mazet, Synlett 2012, 23, 1999;
40. J. García-Fortanet, S. L. Buchwald, Angew. Chem. 2008, 120, 8228
41. Angew. Chem. Int. Ed. 2008, 47, 8108.
42. For other (P,N) ligands with diastereomeric P units, see: a) M. Peer, J. C. de Jong, M. Kiefer, T. Langer, H. Rieck, H. Schell, P. Sennhenn, J. Sprinz, H. Steinhagen, B. Wiese, G. Helmchen, Tetrahedron 1996, 52, 7547
43. S. Kudis, G. Helmchen, Angew. Chem. 1998, 110, 3210
44. Angew. Chem. Int. Ed. 1998, 37, 3047.
45. T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 5139
46. S. Enthaler, G. Erre, K. Junge, J. Holz, ABörne, E. Alberico, I. Nieddu, S. Gladiali, M. Beller, Org. Process Res. Dev. 2007, 11, 568.
47. P. Kasák, K. Mereiter, M. Wildhalm, Tetrahedron: Asymmetry 2005, 16, 3416
48. P. Kasák, V. B. Arion, M. Wildhalm, Tetrahedron: Asymmetry 2006, 17, 3084
49. Q. Dai, W. Li, X. Zhang, Tetrahedron 2008, 64, 6943.
50. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
51. W. Egan, R. Tang, G. Zon, K. Mislow, J. Am. Chem. Soc. 1970, 92, 1442
52. R. D. Baechler, K. Mislow, J. Am. Chem. Soc. 1970, 92, 3090
53. A. Rauk, J. D. Andose, W. G. Frick, R. Tang, K. Mislow, J. Am. Chem. Soc. 1971, 93, 6507
54. K. Mislow, W. Egan, J. Am. Chem. Soc. 1971, 93, 1805.
55. S. E. Cremer, R. J. Chorvat, C. H. Chang, D. W. Davis, Tetrahedron Lett. 1968, 9, 5799
56. K. L. Marsi, J. Am. Chem. Soc. 1969, 91, 4724
57. S. I. Featherman, L. D. Quin, J. Am. Chem. Soc. 1975, 97, 4349
58. G. D. Macdonell, K. D. Berlin, J. R. Baker, S. E. Ealick, D. van der Helm, K. L. Marsi, J. Am. Chem. Soc. 1978, 100, 4535
59. S. M. Bachrach, J. Phys. Chem. 1989, 93, 7780.
60. For an alternative mechanism on a macrocyclic system, see:, M. Stollenz, M. Barbasiewicz, A. J. Nawara-Hultzsch, T. Fiedler, R. M. Laddusaw, N. Bhuvanesh, J. A. Gladysz, Angew. Chem. 2011, 123, 6777
61. Angew. Chem. Int. Ed. 2011, 50, 6647.
62. During the preparation of this manuscript, a remarkable study by Radosevich and co-workers was published. Based on a combined theoretical and electrochemical approach, the authors described the configurational lability of a series of acyclic P-stereogenic phosphines through a single electron oxidation mechanism. See:, K. D. Reichl, D. H. Ess, A. T. Radosevich, J. Am. Chem. Soc. 2013, 135, 9354.
63. Gaussian 09 (Revision A.02), M. J. Frisch et al., Gaussian, Inc., Wallingford, CT, 2009. See the Supporting Information for full reference.
64. T. E. Barder, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 5096.
65. For recent reviews, see: a) X. Cui, K. Burgess, Chem. Rev. 2005, 105, 3272
66. T. L. Church, P. G. Andersson, Coord. Chem. Rev. 2008, 252, 513
67. S. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40, 1402.