The role of symmetry in asymmetric catalysis

Israel Journal of Chemistry

Volumn 52, Issue 7, 2012, Pages 653-662

  Moberg, Christina ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

catalysis; enantioselectivity; homotopicity; paddlewheel; symmetry

Indexed keywords

EID: 84864256627     PISSN: 00212148     EISSN: 18695868     Source Type: Journal    
DOI: 10.1002/ijch.201200020     Document Type: Review

References (64)

1. Oligomeric structures may possess rotational symmetry; for example, see:, B. Wörsdörfer, L. M. Henning, R. Obexer, D. Hilvert, ACS Catal. 2012, 2, 982-985.
2. J. K. Whitesell, Chem. Rev. 1989, 89, 1581-1590.
3. R. Shintani, Y. Ichikawa, K. Takatsu, F.-X. Chen, T. Hayashi, J. Org. Chem. 2009, 74, 869-873
4. S. Anezaki, Y. Yamaguchi, M. Asami, Chem. Lett. 2010, 39, 398-399
5. H. Zhang, F. Fang, F. Xie, H. Yu, G. Yang, W. Zhang, Tetrahedron Lett. 2010, 51, 3119-3122
6. Z. Liu, M. Shi, Organometallics 2010, 29, 2831-2834
7. R. Mariz, A. Poater, M. Gatti, E. Drinkel, J. J. Bürgi, X. Luan, S. Blumentritt, A. Linden, L. Cavallo, R. Dorta, Chem. Eur. J. 2010, 16, 14335-14347
8. Y.-X. Liao, C.-H. Xing, Q.-S. Hu, Org. Lett. 2012, 14, 1544-1547;g) Z.-M.
9. Zhou, Z.-H. Li, X.-Y. Hao, J. Zhang, X. Dong, Y.-Q. Liu, W.-W. Sun, D. Cao, J.-L. Wang, Org. Biomol. Chem. 2012, 10, 2113-2118.
10. C. Moberg, Angew. Chem. Int. Ed. 1998, 37, 248-268
11. S. E. Gibson, M. P. Castaldi, Chem. Commun. 2006, 3045-3062.
12. M. T. Reetz, H. Guo, J.-A. Ma, R. Goddard, R. J. Mynott, J. Am. Chem. Soc. 2009, 131, 4136-4142
13. J. N. Moorthy, S. Saha, Eur. J. Org. Chem. 2010, 6359-6365
14. M. F. Cain, D. S. Glueck, J. A. Golen, A. L. Rheingold, Organometallics 2012, 31, 775-778X
15. F. Wu, C. Min, E. Nyamzundui, H.-B. Zhou, C. Dong, Tetrahedron: Asymmetry 2011, 1640-1643.
16. F. Lake, C. Moberg, Eur. J. Org. Chem. 2002, 3179-3188
17. E. Brulé, Y. Pei, F. Lake, F. Rahm, C. Moberg, Mendeleev Commun. 2004, 276-277
18. Y. Pei, E. Brulé, C. Moberg, Org. Biomol. Chem. 2006, 4, 544-550
19. J. L. Fillol, A. Kruckenberg, P. Scherl, H. Wadepohl, L. H. Gade, Chem. Eur. J. 2011, 17, 14047-14062.
20. C.-T. Chen, S. Bettigeri, S.-S. Weng, V. D. Pawar, Y.-H. Lin, C.-Y. Liu, W.-Z. Lee, J. Org. Chem. 2007, 72, 8175-8185.
21. H. B. Kagan, T.-P. Dang, J. Am. Chem. Soc. 1972, 94, 6429-6433.
22. T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691-1693
23. Q.-L. Zhou, Privileged Chiral Ligands and Catalysts, Wiley-VCH, Weinheim 2011.
24. H. Pellissier in ref 8b, pp.a 333-359.
25. M. Shibasaki, S. Matsunaga in ref 8b, pp.a 295-332.
26. R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345-50
27. T. Ohkuma, N. Kurono in ref 8b, pp.a 1-53.
28. M. J. Burk, Acc. Chem. Res. 2000, 33, 363-372
29. T. P. Clark, C. R. Landis, Tetrahedron: Asymmetry 2004, 15, 2123-2137
30. W. Zhang, X. Zhang in ref 8b, pp.a 55-91.
31. G. Desimoni, G. Faita, K. A. Jørgensen, Chem. Rev. 2006, 106, 3561-3651
32. L.a M. Stanley, M.a P. Sibi in ref 8b, pp.a 171-219.
33. T. R. J. Achard, L. A. Clutterbuck, M. North, Synlett 2005, 1828-1847
34. W.-Z. Zhang, X.-B. Lu in ref 8b, pp 257-293.
35. M. J. Burk, R. L. Harlow, Angew. Chem. Int. Ed. Engl. 1990, 29, 1462-1464.
36. J. Zhou, Y. Tang, Chem. Soc. Rev. 2005, 34, 664-676.
37. L. H. Gade, S. Bellemin-Laponnaz, Chem. Eur. J. 2008, 14, 4142-4152.
38. S. Bellemin-Laponnaz, L. H. Gade, Angew. Chem. Int. Ed. 2002, 41, 3473-3475.
39. M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359-2367.
40. C. Foltz, B. Stecker, G. Marconi, S. Bellemin-Laponnaz, H. Wadepohl, L. H. Gade, Chem. Commun. 2005, 5115-5117.
41. C. Foltz, M. Enders, S. Bellemin-Laponnaz, H. Wadepohl, L. H. Gade, Chem. Eur. J. 2007, 13, 5994-6008.
42. K. Murai, S. Fukushima, S. Hayashi, Y. Takahara, H. Fujioka, Org. Lett. 2010, 12, 964-966.
43. K. Murai, S. Fukushima, A. Nakamura, M. Shimura, H. Fujioka, Tetrahedron 2011, 67, 4862-4868.
44. M. Shi, J.-K. Jiang, Tetrahedron: Asymmetry 1999, 10, 1673-1679.
45. J.-B. Sortais, V. Ritleng, A. Voelklin, A. Holuique, H. Smail, L. Barloy, C. Sirlin, G. K. M. Verzijl, J. A. F. Boogers, A. H. M. dea Vries, J. G. dea Vries, M. Pfeffer, Org. Lett. 2005, 7, 1247-1250.
46. C. Foltz, B. Stecker, G. Marconi, S. Bellemin-Laponnaz, H. Wadepohl, L. H. Gade, Chem. Eur. J. 2007, 13, 9912-9923.
47. For other examples, see:, V. A. Pavlov, Tetrahedron 2008, 64, 1147-1179.
48. S. Zhu, X. Cui, X. P. Zhang, Eur. J. Inorg. Chem. 2012, 430-434.
49. J. Hansen, H. M. L. Davies, Coord. Chem. Rev. 2008, 252, 545-555.
50. V. N. G. Lindsay, W. Lin, A. B. Charette, J. Am. Chem. Soc. 2009, 131, 16383-16385.
51. A. Ghanem, M. G. Gardiner, R. M. Williamson, P. Müller, Chem. Eur. J. 2010, 16, 3291-3295.
52. A. DeAngelis, O. Dmitrenko, G. P. A. Yap, J. M. Fox, J. Am. Chem. Soc. 2009, 131, 7230-7231.
53. A. DeAngelis, D. T. Boruta, J.-B. Lubin, J. N. Plampin, III, G.a P.a A. Yap, J.a M. Fox, Chem. Commun. 2010, 46, 4541-4543.
54. MM2/extended Hückel calculations suggested that the staggered conformation is favored:, H. L. M. Davies, P. R. Bruzinski, D. H. Lake, N. Kong, M. J. Fall, J. Am. Chem. Soc. 1996, 118, 6897-6907.
55. H. T. Bonge, T. Hansen, J. Org. Chem. 2010, 75, 2309-2320.
56. A. S. C. Chan, J. J. Pluth, J. Halpern, J. Am. Chem. Soc. 1980, 102, 5952-5954.
57. L. Milhau, P. J. Guiry, Top. Organomet. Chem. 2012. 38, 95-154
58. B. Trost, J. Org. Chem. 2004, 69, 5813-5837.
59. B. M. Trost, in Catalytic Asymmetric Synthesis (Ed., I. Ojima,), 2nd Ed. Wiley-VCH, New York 2000, pp.a 593-649.
60. G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336-345
61. C.a C. Bausch, A. Pfaltz in ref 8b, pp.a 221-256.
62. K. Inoguchi, S. Sakuraba, K. Achiwa, Synlett 1992, 169-178.
63. H. Adolfsson, K. Wärnmark, C. Moberg, J. Chem. Soc., Chem. Commun. 1992, 1054-1055
64. H. Adolfsson, K. Wärnmark, C. Moberg, unpublished results.