Synthesis and post-resolution modification of new axially chiral ligands for asymmetric catalysis

European Journal of Organic Chemistry

Volumn , Issue 31, 2010, Pages 5996-6004

  Fleming, William J ^a   Müller Bunz, Helge ^a   Guiry, Patrick J ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Asymmetric synthesis; Atropisomerism; Chiral resolution; Chirality; Hydroboration; Ligand design; Palladium

Indexed keywords

EID: 78349277689     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000794     Document Type: Article

References (58)

1. B. M. Trost, Proc. Natl. Acad. Sci. USA 2004, 101, 5348 - 5355.
2. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori, J. Am. Chem. Soc. 1980, 102, 7932 - 7934.
3. I. Ojima, Catalytic Asymmetric Synthesis, 2nd ed.; VCH: Weinheim, 2000.
4. R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994.
5. C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503 - 517.
6. M. McCarthy, P. J. Guiry, Tetrahedron 2001, 57, 3809 - 3844.
7. P. J. Guiry, M. McCarthy, P. M. Lacey, C. P. Saunders, S. Kelly, D. J. Connolly, Curr. Org. Chem. 2000, 4, 835 - 850.
8. Y.-M. Li, F.-Y. Kwong, W.-Y. Yu, A. S. C. Chan, Coord. Chem. Rev. 2007, 251, 2119 - 2144.
9. C. P. Saunders, P. J. Guiry, Adv. Synth. Catal. 2004, 346, 497 - 537.
10. N. W. Alcock, J. M. Brown, D. I. Hulmes, Tetrahedron: Asymmetry 1993, 4, 743 - 756.
11. H. Doucet, E. Fernandez, T. P. Layzell, J. M. Brown, Chem. Eur. J. 1999, 5, 1320 - 1330.
12. J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493 - 4506.
13. C. Chen, X. Li, S. L. Schreiber, J. Am. Chem. Soc. 2003, 125, 10174 - 10175.
14. N. Gommermann, C. Koradin, P. Knochel, Angew. Chem. Int. Ed. 2003, 42, 5763 - 5944.
15. M. McCarthy, R. Goddard, P. J. Guiry, Tetrahedron: Asymmetry 1999, 10, 2797 - 2807.
16. P. M. Lacey, C. McDonnell, P. J. Guiry, Tetrahedron Lett. 2000, 41, 2457 - 2478.
17. D. J. Connolly, P. M. Lacey, M. McCarthy, C. P. Saunders, A. M. Carroll, R. Goddard, P. J. Guiry, J. Org. Chem. 2004, 69, 6572 - 6589.
18. S. P. Flanagan, R. Goddard, P. J. Guiry, Tetrahedron 2005, 61, 9808 - 9821.
19. T. Fekner, H. Müller-Bunz, P. J. Guiry, Org. Lett. 2006, 8, 5109 - 5112.
20. A. C. Maxwell, C. Franc, L. Pouchain, H. Müller-Bunz, P. J. Guiry, Org. Biomol. Chem. 2008, 6, 3848 - 3853.
21. T. Fekner, H. Müller-Bunz, P. J. Guiry, Eur. J. Org. Chem. 2008, 5055 - 5066.
22. M. McCarthy, M. W. Hooper, P. J. Guiry, Chem. Commun. 2000, 1333 - 1334.
23. A. C. Maxwell, S. P. Flanagan, R. Goddard, P. J. Guiry, Tetrahedron: Asymmetry 2010, 21, 1458 - 1473.
24. T. F. Knöpfel, P. Aschwanden, T. Ichikawa, T. Watanabe, E. M. Carreira, Angew. Chem. Int. Ed. 2004, 43, 5971 - 5973.
25. F. Y. Kwong, Q. Yang, T. C. W. Mak, A. S. C. Chan, K. S. Chan, J. Org. Chem. 2002, 67, 2769 - 2777.
26. W. J. Fleming, H. Müller-Bunz, V. Lillo, E. Fernández, P. J. Guiry, Org. Biomol. Chem. 2009, 7, 2520 - 2524.
27. P. J. Guiry, A. M. Carroll, T. P. O'Sullivan, Adv. Synth. Catal. 2005, 347, 609 - 631.
28. C. M. Crudden, D. Edwards, Eur. J. Org. Chem. 2003, 4695 - 4712.
29. A. G. Coyne, P. J. Guiry, Modern Reduction Methods (Ed.:, P. G. Andersson), I. Munslow, Wiley-VCH, 2008, chapter 3, pp. 65-84.
30. P. J. Guiry, ChemCatChem 2009, 1, 233 - 235.
31. D. Cai, J. F. Payack, D. R. Bender, D. L. Hughes, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 7180.
32. 31P NMR spectroscopy) of the bis-phospanylated product were observed.
33. 3, reflections collected: 43701, independent reflections: 20950 [R(int) = 0.0338]. CCDC-745826 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from: The Cambridge Crystallographic Data Centre via.
34. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921 - 2944.
35. B. M. Trost, J. Org. Chem. 2004, 69, 5813 - 5837.
36. Y. M. Malone, P. J. Guiry, J. Organomet. Chem. 2000, 603, 110 - 115.
37. J. P. Cahill, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4301 - 4306.
38. J. P. Cahill, D. Cunneen, P. J. Guiry, Tetrahedron: Asymmetry 1999, 10, 4157 - 4173. For excellent reviews, see
39. B. M. Trost, C. Lee, in: Catalytic Asymmetric Synthesis, 2nd ed. (Ed.:, I. Ojima), Wiley-VCH, Weinheim (Germany), 2000, pp. 593-639.
40. A. Pfaltz, M. Lautens, in: Comprehensive Asymmetric Catalysis (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Tokyo, 1999, vol. 2, pp. 833-884.
41. For optimisation studies see Supporting Information.
42. The endo-isomer is defined as the allyl configuration in which the central allyl proton points in the same direction as the naphthyl-phosphorus bond.
43. Relevant spectra can be found in the Supporting Information.
44. For selected references for mechanistic studies on Pd-catalysed allylic alkylation, see
45. B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. Dietsche, J. Am. Chem. Soc. 1978, 100, 3435 - 3443.
46. T. Hayashi, T. Hagihara, M. Konishi, M. Kumada, J. Am. Chem. Soc. 1983, 105, 7767 - 7768.
47. K. Yonehara, T. Hashizume, K. Mori, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 9374 - 9380.
48. A. Saitoh, K. Achiwa, K. Tanaka, T. Morimoto, J. Org. Chem. 2000, 65, 4227 - 4240.
49. W.-P. Deng, S.-L. You, X.-L. Hou, L.-X. Dai, Y.-H. Yu, W. Xia, J. Sun, J. Am. Chem. Soc. 2001, 123, 6508 - 6510.
50. J. M. Canal, M. Gómez, F. Jiménez, M. Rocamora, G. Muller, E. Duñach, D. Franco, A. Jiménez, F. H. Cano, Organometallics 2000, 19, 966 - 978.
51. P. R. Auburn, P. B. MacKenzie, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2033 - 2046.
52. P. S. Pregosin, R. Salzmann, Coord. Chem. Rev. 1996, 155, 35 - 68.
53. A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1997, 118, 1031 - 1037.
54. J. Sprintz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523 - 1526.
55. C. P. Butts, E. Filali, G. C. Lloyd-Jones, P.-O. Norrby, D. A. Sale, Y. Schramm, J. Am. Chem. Soc. 2009, 131, 9945 - 9957.
56. D. D. Perrin, W. L. F. Armarego, in: Purification of Laboratory Chemicals, Pergamon Press, New York, 1988.
57. W. C. Still, M. Hahn, A. Mitra, J. Org. Chem. 1978, 43, 2923 - 2925.
58. J. Sprintz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769 - 1772.