Regioselectivity in the Cu(I)-catalyzed [4 + 2]-cycloaddition of 2-nitrosopyridine with unsymmetrical dienes

Journal of Organic Chemistry

Volumn 79, Issue 12, 2014, Pages 5617-5626

  Tran, Anh T ^a   Liu, Peng ^b   Houk, K N ^b   Nicholas, Kenneth M ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; OLEFINS; REGIOSELECTIVITY;

CATALYZED REACTIONS; COORDINATION EFFECTS; ELECTRON TRANSFER; ENERGY DIFFERENCES; ORBITAL INTERACTION; QUANTITATIVE AGREEMENT; TRANSITION STATE; UNCATALYZED REACTIONS;

COPPER COMPOUNDS;

1 PHENYLBUTADIENE; 1,3 PENTADIENE; 2 NITROSOPYRIDINE; 2,4 HEXADIENOL; ALKADIENE; CUPROUS ION; NITROSO DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AFFINITY LABELING; ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CYCLOADDITION; ELECTRON TRANSPORT; ELECTROSPRAY MASS SPECTROMETRY; PHASE TRANSITION; REGIOSELECTIVITY; THERMODYNAMICS;

EID: 84903177982     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5005907     Document Type: Article

References (56)

1. Kirby, G. W.; Nazeer, M. J. Chem. Soc., Perkin Trans. 1 1993, 13, 1397-402
2. Freer, A. A.; Islam, M. A.; Kirby, G. W.; Mahajan, M. P. J. Chem. Soc., Perkin Trans. 1 1991, 5, 1001-1007
3. Corrie, J. E. T.; Kirby, G. W.; Mackinnon, J. W. M. J. Chem. Soc., Perkin Trans. 1 1985, 4, 883-886
4. Kirby, G. W.; Bentley, K. W.; Horsewood, P.; Singh, S. J. Chem. Soc., Perkin Trans. 1 1979, 12, 3064-3066
5. Li, J.; Lang, F.; Ganem, B. J. Org. Chem. 1998, 63, 3403
6. Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem. 1998, 63, 8397
7. Jana, C. K.; Studer, A. Chem.-Eur. J. 2008, 14, 6326
8. Li, F.; Brogan, J. B.; Gage, J. L.; Zhang, D.; Miller, M. J. J. Org. Chem. 2004, 69, 4538
9. Yamamoto, H.; Kawasaki, M. Bull. Chem. Soc. Jpn. 2007, 80, 595
10. Bodnar, B. S.; Miller, M. J. Angew. Chem., Int. Ed. 2011, 50, 5630
11. Iwasa, S.; Ahmad, F.; Nishiyama, H. Mini-Rev. Org. Chem. 2005, 2, 157
12. Krchnák, V.; Moellmann, U.; Dahse, H.-M.; Miller, M. J. J. Comb. Chem. 2008, 10, 104
13. Lin, W.; Gupta, A.; Kim, K. H.; Mendel, D.; Miller, M. J. Org. Lett. 2009, 11, 449
14. Li, F.; Yang, B.; Miller, M. J.; Zajicek, J.; Noll, B. C.; Möllmann, U.; Dahse, H.-M.; Miller, P. A. Org. Lett. 2007, 9, 2923
15. Labaziewicz, H. L.; Karl, R.; Kejonen, T. H. Heterocycles 1989, 29, 2327
16. Yang, B.; Miller, P. A.; Möllmann, U.; Miller, M. J. Org. Lett. 2009, 11, 2828
17. Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128
18. Yamamoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 7082
19. Chow, C. P.; Shea, K. J. J. Am. Chem. Soc. 2005, 127, 3678
20. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360
21. Flower, K. R.; Lightfoot, A. P.; Wan, H.; Whiting, A. J. Chem. Soc., Perkin Trans. 1 2002, 18, 2058
22. Leach, A. G.; Houk, K. N. J. Org. Chem. 2001, 66, 5192
23. McCarrick, M. A.; Wu, Y. D.; Houk, K. N. J. Org. Chem. 1993, 58, 3330
24. Leach, A. G.; Houk, K. N. Chem. Commun. 2002, 0, 1243
25. Jana, C. K.; Grimme, S.; Studer, A. Chem.-Eur. J. 2009, 15, 9078
26. Jana, C. K.; Studer, A. Angew. Chem., Int. Ed. 2007, 46, 6542
27. Bollans, L.; Bacsa, J.; OFarrell, D. A.; Waterson, S.; Stachulski, A. V. Tetrahedron Lett. 2010, 51, 2160
28. Calvet, G.; Blanchard, N.; Kouklovsky, C. Synthesis 2005, 2005, 3346
29. Miller, C. A.; Batey, R. A. Org. Lett. 2004, 6, 699
30. Yang, B.; Lin, W.; Krchnak, V.; Miller, M. J. Tetrahedron Lett. 2009, 50, 5879
31. Resmini, M.; Meekel, A. A. P.; Pandit, U. K. Pure Appl. Chem. 1996, 68, 2025
32. Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571
33. Reymond, S. B.; Cossy, J. Chem. Rev. 2008, 108, 5359
34. Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Eur. J. Org. Chem. 2001, 439
35. Markó, I. E.; Evans, G. R.; Seres, P.; Chellé, I.; Janousek, Z. Pure Appl. Chem. 1996, 68, 113
36. Matsumoto, M.; Estes, D.; Nicholas, K. M. Eur. J. Inorg. Chem. 2010, 1847
37. Miller, B. L., Ed. Dynamic Combinatorial Chemistry In Drug Discovery, Bioorganic Chemistry and Materials Science; Wiley: Hoboken, NJ, 2009.
38. Ladame, S. Org. Biomol. Chem. 2008, 6, 219
39. Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J. L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652
40. Lehn, J.-M. Chem. Soc. Rev. 2007, 36, 151
41. Gasparini, G.; Molin, M. D.; Prins, L. J. Eur. J. Org. Chem. 2010, 2429
42. Breuil, P.-A. R.; Reek, J. N. H. Dynamic Combinatorial Chemistry for Catalytic Applications. In Dynamic Combinatorial Chemistry; Reek, J. N. H.; Otto, S., Eds.; Wiley-VCH: Weinheim, Germany, 2010.
43. Kannappan, R.; Matsumoto, M.; Hallren, J.; Nicholas, K. M. J. Mol. Catal. A: Chem. 2011, 339, 72
44. Kannappan, R.; Nicholas, K. M. ACS Comb. Sci. 2013, 15, 90
45. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
46. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
47. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
48. Scalmani, G.; Frisch, M. J. J. Chem. Phys. 2010, 132, 114110
49. Lam, Y.-H.; Cheong, P. H.-Y.; Blasco Mata, J. M.; Stanway, S. J.; Gouverneur, V.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 1947
50. Pieniazek, S. N.; Clemente, F. R.; Houk, K. N. Angew. Chem., Int. Ed. 2008, 47, 7746
51. Siegert, U.; Hahn, H.; Lang, H. Inorg. Chim. Acta 2010, 363, 944
52. Nitschke, J. R. Acc. Chem. Res. 2007, 40, 103
53. Riesgo, E.; Hu, Y.-Z.; Bouvier, F.; Thummel, R. P. Inorg. Chem. 2001, 40, 2541
54. Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127
55. Taylor, E. C.; Tseng, C. P.; Rampal, J. B. J. Org. Chem. 1982, 47, 552
56. Lishchynskyi, A.; Muñiz, K. Chem.-Eur. J. 2012, 18, 2212