SIAPhos: Phosphorylated sulfonimidamides and their use in iridium-catalyzed asymmetric hydrogenations of sterically hindered cyclic enamides

Advanced Synthesis and Catalysis

Volumn 354, Issue 1, 2012, Pages 59-64

  Patureau, Frederic W ^a,d   Worch, Christin ^b   Siegler, Maxime A ^c   Spek, Anthony L ^c   Bolm, Carsten ^b   Reek, Joost N H ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b RWTH AACHEN UNIVERSITY   (Germany)

^c UTRECHT UNIVERSITY   (Netherlands)

^d Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Asymmetric hydrogenation; Iridium; Phosphorylated sulfonimidamides (SIAPhos); SIAPhos (phosphorylated sulfonimidamides); Sulfonimidamides; Sulfur chirality

Indexed keywords

EID: 84856895123     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100692     Document Type: Article

References (71)

1. J. G. de Vries and C. J. Elsevier, The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, 2007
2. H.-U. Blaser, B. Pugin, F. Spindler, M. Thommen, Acc. Chem. Res. 2007, 40, 1240
3. H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103
4. I. D. Gridnev, T. Imamoto, Chem. Commun. 2009, 7447
5. J. K. Whitesell, Chem. Rev. 1989, 89, 1581
6. J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713.
7. J. M. Brown, P. L. Evans, Tetrahedron 1988, 44, 4905.
8. For successful neutral rhodium and iridium complexes, see: a) F. W. Patureau, S. de Boer, M. Kuil, J. Meeuwissen, P-A. B. Breuil, M. A. Siegler, A. L. Spek, A. J. Sandee, B. de Bruin, J. N. H. Reek, J. Am. Chem. Soc. 2009, 131, 6683
9. F. Giacomina, A. Meetsma, L. Panella, L. Lefort, A. H. M. de Vries, J. G. de Vries, Angew. Chem. 2007, 119, 1519
10. Angew. Chem. Int. Ed. 2007, 46, 1497.
11. For analogous strategies in Ir asymmetric hydrogenation, see also: c) G. Erre, S. Enthaler, K. Junge, D. Addis, M. Beller, Adv. Synth. Catal. 2009, 351, 1437
12. S. Enthaler, G. Erre, K. Junge, K. Schrčder, D. Addis, D. Michalik, M. Hapke, D. Redkin, M. Beller, Eur. J. Org. Chem. 2008, 3352.
13. For Ir asymmetric hydrogenation examples of cyclic enamides with C2-symmetrical phosphoramidites see also: e) G.-H. Hou, J.-H. Xie, P.-C. Yan, Q-L. Zhou, J. Am. Chem. Soc. 2009, 131, 1366.
14. For indicative examples of phosphoramidites in IrCl-based neutral catalysis, see also: f) T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 15164
15. F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426
16. C. A. Kiener, C. Shu, C. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14272
17. A. Leitner, S. Shekhar, M. J. Pouy, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 15506
18. G. Lipowsky, N. Miller, G. Helmchen, Angew. Chem. 2004, 116, 4695
19. Angew. Chem. Int. Ed. 2004, 43, 4595.
20. For reviews, see: a) V. A. Pavlov, Tetrahedron 2008, 64, 1147
21. K. C. Bhowmick, N. N. Joshi, Tetrahedron: Asymmetry 2006, 17, 1901
22. J. Wassenaar, J. N. H. Reek, Org. Biomol. Chem. 2011 ,9, 1704
23. H. Fernandez-Perez, P. Etayo, A. Panossian, A. Vidal-Ferran Chem. Rev. 2011, 111, 2119
24. F. Boeda, T. Beneyton, C. Crávisy, Mini-Rev. Org. Chem. 2008, 5, 96
25. H. A. McManus, P. J. Guiry, Chem. Rev. 2004, 104, 4151.
26. For some examples: g) G. Francio, F. Faraone, W. Leitner, Angew. Chem. 2000, 112, 1486
27. Angew. Chem. Int. Ed. 2000, 39, 1428
28. X. P. Hu, Z. Zheng, Org. Lett. 2004, 6, 3585
29. X. P. Hu, Z. Zheng, Org. Lett. 2005, 7, 419
30. Q. H. Zeng, X. P. Hu, Z. C. Duan, X. M. Liang, Z. Zheng, Tetrahedron: Asymmetry 2005, 16, 1233
31. J. D. Huang, X. P. Hu, Z. C. Duan, Q. H. Zeng, S. B. Yu, J. Deng, D. Y. Wang, Z. Zheng, Org. Lett. 2006, 8, 4367
32. D. Y. Wang, X. P. Hu, J. D. Huang, J. Deng, S. B. Yu, Z. C. Duan, X. F. Xu, Z. Zheng, Angew. Chem. 2007, 119, 7956
33. Angew. Chem. Int. Ed. 2007, 46, 7810
34. M. Qiu, X. P. Hu, D. Y. Wang, J. Deng, J. D. Huang, S. B. Yu, Z. C. Duan, Z. Zheng, Adv. Synth. Catal. 2008, 350, 1413
35. S. B. Yu, J.-D. Huang, D. Y. Wang, X. P. Hu, J. Deng, Z. C. Duan, Z. Zheng, Tetrahedron: Asymmetry 2008, 19, 1862
36. K. A. Vallianatou, I. D. Kostas, J. Holz, A. Bčrner, Tetrahedron Lett. 2006, 47, 7947
37. Y. Yan, X. Zhang, J. Am. Chem. Soc. 2006, 128, 7198
38. X. Zhang, B. Cao, Y. Yan, S. Yu, B. Ji, X. Zhang, Chem. Eur. J. 2010, 16, 871
39. Z.C. Duan, X. P. Hu, J. Deng, S. B. Yu, D. Y. Wang, Z. Zheng, Tetrahedron: Asymmetry 2009, 20, 588
40. M. Qiu, D. Y. Wang, X. P. Hu, J. D. Huang, S. B. Yu, J. Deng, Z. C. Duan, Z. Zheng, Tetrahedron: Asymmetry 2009, 20, 210
41. S. B. Yu, X. P. Hu, J. Deng, D. Y. Wang, Z. C. Duan, Z. Zheng, Tetrahedron: Asymmetry 2009, 20, 621
42. J. Wassenaar, J. N. H. Reek, Dalton Trans. 2007, 3750
43. J. Wassenaar, M. Kuil, J. N. H. Reek, Adv. Synth. Catal. 2008, 350, 1610
44. J. Wassenaar, J. N. H. Reek, J. Org. Chem. 2009, 74, 8403
45. C. Darcel, D. Moulin, J-C. Henry, M. Lagrelette, P. Richard, P. D. Harvey, S. Juge, Eur. J. Org. Chem. 2007, 2078
46. J. Wassenaar, E. Jansen, W. J. van Zeist, F. M. Bickelhaupt, M. A. Siegler, A. L. Spek, J. N. H. Reek, Nature Chem. 2010, 2, 417
47. J. Wassenaar, M. Kuil, M. Lutz, A. L. Spek, J. N. H. Reek, Chem. Eur. J. 2010,16, 6509.
48. For an indicative example of a neutral hydrogenation catalyst employing a C1-symmetrical chiral ligand see: W. S. Knowles, M. J. Sabacky, J. Chem. Soc. Chem. Commun. 1968, 1445.
49. W. Tang, Y. Chi, X. Zhang, Org. Lett. 2002, 4, 1695
50. Z. Zhang, G. Zhu, Q. Jiang, D. Xiao, X. Zhang, J. Org. Chem. 1999, 64, 1774
51. J. L. Renaud, P. Dupau, A-E. Hay, M. Guingouain, P. H. Dixneuf, C. Bruneau, Adv. Synth. Catal. 2003, 345, 230
52. X-B. Jiang, L. Lefort, P. E. Goudriaan, A. H. M. de Vries, P. W. N. M. van Leeuwen, J. G. de Vries, J. N. H. Reek, Angew. Chem. 2006, 118, 1245
53. Angew. Chem. Int. Ed. 2006, 45, 1223
54. P. Dupau, C. Bruneau, P. H. Dixneuf, Adv. Synth. Catal. 2001, 343, 331
55. M. C. Jetter, M. A. Youngman, J. J. McNally, M. E. McDonnell, S-P. Zhang, A. E. Dubin, N. Nasser, E. E. Codd, C. M. Flores, S. L. Dax, Bioorg. Med. Chem. Lett. 2007, 17, 6160
56. M. A. Youngman, N. M. Willard, S. L. Dax, J. J. McNally, Synth. Commun. 2003, 33, 2215
57. J. Meeuwissen, M. Kuil, A. M. van der Burg, A. J. Sandee, J. N. H. Reek, Chem. Eur. J. 2009, 15, 10272.
58. C. Liang, F. Collet, F. Robert-Peillard, P. Müller, R. H. Dodd, P. Dauban, J. Am. Chem. Soc. 2008, 130, 343
59. C. Liang, F. Robert-Peillard, C. Fruit, P. Müller, R. H. Dodd, P. Dauban, Angew. Chem. 2006, 118, 4757
60. Angew. Chem. Int. Ed. 2006, 45, 4641
61. C. Fruit, F. Robert-Peillard, G. Bernardinelli, P. Müller, R. H. Dodd, P. Dauban, Tetrahedron: Asymmetry 2005, 16, 3484
62. C. Worch, C. Bolm, Synthesis 2007, 1355
63. C. Worch, C. Bolm, Synthesis 2008, 739
64. S. Azzaro, L. Fensterbank, E. Lacote, M. Malacria, Synlett 2008, 2253
65. C. Worch, I. Atodiresei, G. Raabe, C. Bolm, Chem. Eur. J. 2010, 16, 677.
66. For an asymmetric organocatalysis, see: C. Worch, C. Bolm, Synlett 2009, 2425.
67. F. W. Patureau, M. Kuil, A. J. Sandee, J. N. H. Reek, Angew. Chem. 2008, 120, 3224
68. Angew. Chem. Int. Ed. 2008, 47, 3180.
69. Highlight: b) H. Yamamoto, P. Li, Synfacts 2008, 7, 0721
70. P-A. R. Breuil, F. W. Patureau, J. N. H. Reek, Angew. Chem. 2009, 121, 2196;
71. Angew. Chem. Int. Ed. 2009, 48, 2162.