Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins

Journal of the American Chemical Society

Volumn 136, Issue 48, 2014, Pages 16748-16751

  Yang, Junfeng ^a   Yoshikai, Naohiko ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ENANTIOSELECTIVITY; ISOTOPES; KETONES;

C-H ACTIVATION; CATALYTIC SYSTEM; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; HYDROACYLATION; INTRAMOLECULAR HYDROACYLATION; KINETIC ISOTOPE EFFECTS; RATE-LIMITING STEPS;

COBALT;

2 ACYLBENZALDEHYDE DERIVATIVE; 2 ALKENYLBENZALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; BENZALDEHYDE DERIVATIVE; COBALT; INDANONE DERIVATIVE; KETONE DERIVATIVE; PHTHALIDE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYST; CHEMICAL PARAMETERS; CHEMICAL REACTION KINETICS; CHIRALITY; CONTROLLED STUDY; COVALENT BOND; ENANTIOSELECTIVITY; INTRAMOLECULAR HYDROACYLATION; ISOTOPE LABELING; KINETIC ISOTOPE EFFECT; REACTION ANALYSIS;

EID: 84915766740     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja509919x     Document Type: Article

References (56)

1. Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 1869
2. Willis, M. C. Chem. Rev. 2010, 110, 725
3. Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202
4. Trost, B. M.; Krische, M. J. Synlett 1998, 1
5. Murphy, S. K.; Dong, V. M. Chem. Commun. 2014, 50, 13645
6. Gonzaléz-Rodríguez, C.; Pawley, R. J.; Chaplin, A. B.; Thompson, A. L.; Weller, A. S.; Willis, M. C. Angew. Chem., Int. Ed. 2011, 50, 5134
7. Hoffman, T. J.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 10670
8. Lenden, P.; Entwistle, D. A.; Willis, M. C. Angew. Chem., Int. Ed. 2011, 50, 10657
9. Murphy, S. K.; Coulter, M. M.; Dong, V. M. Chem. Sci. 2012, 3, 355
10. Chaplin, A. B.; Hooper, J. F.; Weller, A. S.; Willis, M. C. J. Am. Chem. Soc. 2012, 134, 4885
11. von Delius, M.; Le, C. M.; Dong, V. M. J. Am. Chem. Soc. 2012, 134, 15022
12. Hooper, J. F.; Young, R. D.; Weller, A. S.; Willis, M. C. Chem.-Eur. J. 2013, 19, 3125
13. Castaing, M.; Wason, S. L.; Estepa, B.; Hooper, J. F.; Willis, M. C. Angew. Chem., Int. Ed. 2013, 52, 13280
14. Murphy, S. K.; Bruch, A.; Dong, V. M. Angew. Chem., Int. Ed. 2014, 53, 2455
15. Ghosh, A.; Stanley, L. M. Chem. Commun. 2014, 50, 2765
16. Arnold, J. S.; Mwenda, E. T.; Nguyen, H. M. Angew. Chem., Int. Ed. 2014, 53, 3688
17. Kou, K. G. M.; Le, D. N.; Dong, V. M. J. Am. Chem. Soc. 2014, 136, 9471
18. Gao, K.; Yoshikai, N. Acc. Chem. Res. 2014, 47, 1208
19. Obligacion, J. V.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 4133
20. Santhoshkumar, R.; Mannathan, S.; Cheng, C.-H. Org. Lett. 2014, 16, 4208
21. Tan, B.-H.; Yoshikai, N. Org. Lett. 2014, 16, 3392
22. Friedfeld, M. R.; Shevlin, M.; Hoyt, J. M.; Krska, S. W.; Tudge, M. T.; Chirik, P. J. Science 2013, 342, 1076
23. Yoshino, T.; Ikemoto, H.; Matsunaga, S.; Kanai, M. Angew. Chem., Int. Ed. 2013, 52, 2207
24. Karthikeyan, J.; Masilamani, J.; Cheng, C.-H. Chem.-Eur. J. 2010, 16, 8989
25. Hess, W.; Treutwein, J.; Hilt, G. Synthesis 2008, 3537
26. Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307
27. Varela, J. A.; Saá, C. Chem. Rev. 2003, 103, 3787
28. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Catal. A 1995, 104, 17
29. Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165
30. Lenges, C. P.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 6965
31. Chen, Q.-A.; Kim, D. K.; Dong, V. M. J. Am. Chem. Soc. 2014, 136, 3772
32. Vinogradov, M. G.; Tuzikov, A. B.; Nikishin, G. I.; Shelimov, B. N.; Kazansky, V. B. J. Organomet. Chem. 1988, 348, 123
33. For a review of cobalt-catalyzed enantioselective reactions, see: Pellissier, H.; Clavier, H. Chem. Rev. 2014, 114, 2775
34. Sawano, T.; Ashouri, A.; Nishimura, T.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 18936
35. Wei, C.-H.; Mannathan, S.; Cheng, C.-H. Angew. Chem., Int. Ed. 2012, 51, 10592
36. Wei, C.-H.; Mannathan, S.; Cheng, C.-H. J. Am. Chem. Soc. 2011, 133, 6942
37. Sharma, R. K.; RajanBabu, T. V. J. Am. Chem. Soc. 2010, 132, 3295
38. Phan, D. H. T.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608
39. Kundu, K.; McCullagh, J. V.; Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042
40. Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci. 2011, 2, 407
41. Shen, Z.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077
42. Shen, Z.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916
43. Phan, D. H.; Kou, K. G. M.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16354
44. Coulter, M. M.; Kou, K. G. M.; Galligan, B.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16330
45. Shibata, Y.; Tanaka, K. J. Am. Chem. Soc. 2009, 131, 12552
46. Coulter, M. M.; Dornan, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932
47. Osborne, J. D.; Randell-Sly, H. E.; Currie, G. S.; Cowley, A. R.; Willis, M. C. J. Am. Chem. Soc. 2008, 130, 17232
48. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821
49. Taura, Y.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron 1991, 47, 4879
50. Fiebig, L.; Kuttner, J.; Hilt, G.; Schwarzer, M. C.; Frenking, G.; Schmalz, H.-G.; Schäfer, M. J. Org. Chem. 2013, 78, 10485
51. Omura, S.; Fukuyama, T.; Murakami, Y.; Okamoto, H.; Ryu, I. Chem. Commun. 2009, 6741
52. Murphy, S. K.; Dong, V. M. J. Am. Chem. Soc. 2013, 135, 5553
53. Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946
54. Barnhart, R. W.; Bosnich, B. Organometallics 1995, 14, 4343
55. Roy, A. H.; Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 2007, 129, 2082
56. Hyatt, I. F. D.; Anderson, H. K.; Morehead, A. T., Jr.; Sargent, A. L. Organometallics 2008, 27, 135