Isomerization of terminal epoxides by a [Pd-H] catalyst: A combined experimental and theoretical mechanistic study

Journal of the American Chemical Society

Volumn 135, Issue 16, 2013, Pages 6177-6183

  Vyas, Devendra J ^a   Larionov, Evgeny ^a   Besnard, Céline ^a   Guénée, Laure ^a   Mazet, Clément ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE; PALLADIUM HYDRIDE; SYNTHETIC UTILITY; TERMINAL EPOXIDE; THEORETICAL MECHANISTIC STUDIES;

ENANTIOSELECTIVITY; HYDRIDES; ISOMERIZATION; ISOMERS; PALLADIUM COMPOUNDS;

CATALYSTS;

PALLADIUM; PALLADIUM HYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; ISOMERIZATION;

EID: 84876714293     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja400325w     Document Type: Article

References (71)

1. Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483-1506
2. Silva, L. F., Jr. Tetrahedron 2002, 58, 9137-9161
3. Bando, T.; Shishido, K. Chem. Commun. 1996, 1357-1358
4. Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749-3752
5. Kinura, T.; Yamamoto, N.; Suzuki, Y.; Kawano, K.; Norimine, Y.; Ito, K.; Nagato, S.; Iimura, Y.; Yonaga, M. J. Org. Chem. 2002, 67, 6228-6231
6. House, H. O. J. Am. Chem. Soc. 1954, 77, 3070-3075
7. Naqvi, S. M.; Horowitz, J. P.; Filler, R. J. Am. Chem. Soc. 1957, 79, 6283-6286
8. Meinwald, J.; Labana, S. S.; Chadha, M. S. J. Am. Chem. Soc. 1962, 85, 582-585
9. Miyashita, A.; Shimada, T.; Sugawara, A.; Nohira, H. Chem. Lett. 1986, 1323-1326
10. Ranu, B. C.; Jana, U. J. Org. Chem. 1998, 63, 8212-8216
11. Anderson, A. M.; Blazek, J. M.; Garg, P.; Payne, B. J.; Mohan, R. S. Tetrahedron Lett. 2000, 41, 1527-1530
12. Martinez, F.; Del Campo, C.; Llama, E. F. J. Chem. Soc., Perkin Trans. 1 2000, 1749-1751
13. Kamaré, I.; Tommasino, M. L.; Lemaire, M. Tetrahedron Lett. 2003, 44, 7687-7689
14. Procopio, A.; Dalpozzo, R.; De Nino, A.; Nardi, M.; Sindona, G.; Tagarelli, A. Synlett 2004, 2633-2635
15. Robinson, M. W. C.; Pillinger, K. S.; Graham, A. E. Tetrahedron Lett. 2006, 47, 5919-5921
16. Ertürk, E.; Göllü, M.; Demir, A. S. Tetrahedron 2010, 66, 2373-2377
17. Robinson, M. W. C.; Pillinger, K. S.; Mabbett, L.; Timms, D. A.; Graham, A. E. Tetrahedron 2010, 66, 8377-8382
18. Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431-6432
19. Suda, K.; Kikkawa, T.; Nakajima, S.-i.; Takanami, T. J. Am. Chem. Soc. 2004, 126, 9554-9555
20. Suda, K.; Nakajima, S.-i.; Satoh, Y.; Takanami, T. Chem. Commun. 2009, 1255-1257
21. Hrdina, R.; Müller, C. E.; Wende, R. C.; Lippert, K. M.; Benassi, M.; Spengler, B.; Schreiner, P. R. J. Am. Chem. Soc. 2011, 133, 7624-7627
22. Feng, X.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2831-2836
23. Naruse, Y.; Esaki, T.; Yamamoto, Y. Tetrahedron 1988, 44, 4747-4756
24. Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777-3779
25. Sodergren, M. J.; Bertilsson, S. K.; Andersson, P. G. J. Am. Chem. Soc. 2000, 122, 6610-6618
26. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384
27. Asami, M. J. Synth. Org. Chem. Jpn. 1996, 54, 188-199
28. O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439-1457
29. Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854-2967
30. Enders, D.; Wortmann, L.; Peters, R. Acc. Chem. Res. 2000, 33, 157-169
31. Nozaki, K. In Comprehensive Asymmetric Catalysis, Vol. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Chapter 11.
32. Claver, C.; van Leuween, P. N. M. W. In Rhodium-catalyzed Hydroformylation; van Leuween, P. N. M. W.; Claver, C., Eds.; Kluwer Academic Publishers: Boston, 2000; Chapter 5.
33. Klosin, J.; Landis, C. R. Acc. Chem. Res. 2007, 40, 1251-1259
34. Guai, A.; Godard, C.; Castillón, S.; Claver, C. Tetrahedron: Asymmetry 2010, 15, 1135-1146
35. Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451
36. Ibrahem, I.; Córdova, A. Angew. Chem., Int. Ed. 2006, 45, 1952-1956
37. Beeson, T. D.; Mastraccio, A.; Hong, J. B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582-585
38. Xie, H.; Zu, L.; Li, H.; Wang, J.; Wang, W. J. Am. Chem. Soc. 2007, 129, 10886-10894
39. Rios, R.; Sundén, H.; Vesely, J.; Zhao, G.-L.; Eriksson, L.; Córdova, A. Adv. Synth. Catal. 2007, 349, 1028-1032
40. Rios, R.; Vesely, J.; Sundén, H.; Ibrahem, I.; Zhao, G.-L.; Córdova, A. Tetrahedron Lett. 2007, 48, 5835-5839
41. Hodgson, D. M.; Kaka, N. S. Angew. Chem., Int. Ed. 2008, 47, 9958-9960
42. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77-80
43. Allen, A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 4260-4263
44. Skucas, E.; MacMillan, D.W. C. J. Am. Chem. Soc. 2012, 134, 9090-9093
45. Shaikh, R. R.; Mazzanti, A.; Petrini, M.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8707-8710
46. Milstein, D.; Buchman, O.; Blum, J. J. Org. Chem. 1977, 42, 2299-2309
47. Aye, K.-T.; Gelmini, L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464-2465
48. Hirai, A.; Yu, X.-Q.; Tonooka, T.; Miyashita, M. Chem. Commun. 2003, 2482-2483
49. Beaver, M. G.; Jamison, T. F. Org. Lett. 2011, 13, 4140-4143
50. Shaghafi, M. B.; Grote, R. E.; Jarvo, E. R. Org. Lett. 2011, 13, 5188-5191
51. Nielsen, D. K.; Doyle, A. G. Angew. Chem., Int. Ed. 2011, 50, 6056-6059
52. Lin, B. L.; Clough, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 2890-2891
53. Wolfe, J. P.; Ney, J. E. Org. Lett. 2003, 5, 4607-4610
54. Ney, J. E.; Wolfe, J. P. J. Am. Chem. Soc. 2006, 128, 15415-15422
55. Huang, C.-Y; Doyle, A. G. J. Am. Chem. Soc. 2012, 134, 9541-9544
56. Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195-7196
57. Kim, J.-H.; Kulawiec, R. J. J. Org. Chem. 1996, 61, 7656-7657
58. Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1997, 62, 6547-6561
59. Kulasegaram, S.; Kulawiec, R. J. Tetrahedron 1998, 54, 1361-1374
60. Perez, P. J.; Calabrese, J. C.; Bunel, E. E. Organometallics 2001, 20, 337-345
61. For an alternative synthesis, see: Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1655-1664
62. CCDC 905952 for complex 3 contains the supplementary crystallographic data for this article. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre (CCDC) at www.ccdc.cam.ac.uk/data- request/cif. The structures in Figures 1 and 6 were generated with CYLview: Legault, C. Y. CYLview, version 1.0.561b; Université de Sherbrooke: Sherbrooke, QC, 2009; http://www.cylview.org.
63. For examples of synthetic derivatizations of methoxy-substituted aryl compounds, see: Li, B. J.; Yu, D.-G.; Sun, C.-L.; Shi, Z.-J. Chem.-Eur. J. 2011, 17, 1728-1759
64. Albéniz, A. C.; Espinet, P.; López-Fernández, R.; Sen, A. J. Am. Chem. Soc. 2002, 124, 11278-11279
65. Tan, E. H. P.; Lloyd-Jones, G. C.; Harvey, J. N.; Lennox, A. J. J.; Mills, B. M. Angew. Chem., Int. Ed. 2011, 50, 9602-9606
66. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-331
67. Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 1, 5-26
68. Steinreiber, J.; Faber, K.; Griengl, H. Chem.-Eur. J. 2008, 14, 8060-8072
69. Frisch, M. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
70. LANL2 ECP: Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283
71. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3094