Nickel(0)-catalyzed [2 + 2 + 1] carbonylative cycloaddition of imines and alkynes or norbornene leading to γ-lactams

Journal of the American Chemical Society

Volumn 136, Issue 45, 2014, Pages 15877-15880

  Hoshimoto, Yoichi ^a   Ohata, Tomoya ^a   Sasaoka, Yukari ^a   Ohashi, Masato ^a   Ogoshi, Sensuke ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CATALYSIS; CYCLOADDITION; HYDROCARBONS; NITROGEN COMPOUNDS;

CYCLOADDITION REACTION; HIGH YIELD; NORBORNENES;

NICKEL;

ACETYLENE DERIVATIVE; ALKYNE DERIVATIVE; BENZENESULFONAMIDE DERIVATIVE; BETA LACTAM DERIVATIVE; CARBONYL DERIVATIVE; FORMIC ACID DERIVATIVE; IMINE; NICKEL; NORBORNENE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; 2-NORBORNENE; ALKYNE; NORBORNANE DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYSIS; CRYSTAL STRUCTURE; CYCLIZATION; CYCLOADDITION; NUCLEOPHILICITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION;

ALKYNES; CATALYSIS; CYCLOADDITION REACTION; IMINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NICKEL; NORBORNANES;

EID: 84910019765     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja509171a     Document Type: Article

References (55)

1. Crawley, M. L.; Trost, B. M. Applications of transition metal catalysis in drug discovery and development: an industrial perspective; John Wiley & Sons: Hoboken, NJ, 2012.
2. Gamzu, E. R.; Hoover, T. M.; Gracon, S. I. Drug Dev. Res. 1989, 18, 177
3. Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D.; Katayama, C.; Iwadare, S.; Shizuri, Y.; Mitomo, R.; Nakano, F.; Matsuzaki, A. Tetrahedron Lett. 1985, 26, 1073
4. Masse, C. E.; Morgan, A. J.; Adams, J.; Panek, J. S. Eur. J. Org. Chem. 2000, 2513
5. Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355
6. Guntern, A.; Ioset, J. R.; Queiroz, E. F.; Sándor, P.; Foggin, C. M.; Hostettmann, K. J. Nat. Prod. 2003, 66, 1550
7. Stuk, T. L.; Assink, B. K.; Bates, R. C., Jr.; Erdman, D. T.; Fedij, V.; Jennings, S. M.; Lassig, J. A.; Smith, R. J.; Smith, T. L. Org. Process Res. Dev. 2003, 7, 851
8. Manam, R. R.; Teisan, S.; White, D. J.; Nicholson, B.; Grodberg, J.; Neuteboom, S. T. C.; Lam, K. S.; Mosca, D. A.; Lloyd, G. K.; Potts, B. C. M. J. Nat. Prod. 2005, 68, 240
9. Okazaki, Y.; Ishizuka, A.; Ishihara, A.; Nishioka, T.; Iwamura, H. J. Org. Chem. 2007, 72, 3830
10. Ng, P. Y.; Tang, Y.; Knosp, W. M.; Stadler, H. S.; Shaw, J. T. Angew. Chem., Int. Ed. 2007, 46, 5352
11. Fenical, W.; Jensen, P. R.; Palladino, M. A.; Lam, K. S.; Lloyd, G. K.; Potts, B. C. Bioorg. Med. Chem. 2009, 17, 2175
12. Tan, D. Q.; Atherton, A. L.; Smith, A. J.; Soldi, C.; Hurley, K. A.; Fettinger, J. C.; Shaw, J. T. ACS Comb. Sci. 2012, 14, 218
13. Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 116, 2139
14. Chang, T. T.; More, S. V.; Lu, I.-H.; Hsu, J.-C.; Chen, T.-J.; Jen, Y. C.; Lu, C.-K.; Li, W.-S. Eur. J. Med. Chem. 2011, 46, 3810
15. Li, S.; Qiu, S.; Yao, P.; Sun, H.; Fong, H. H. S.; Zhang, H. Evid. Based Complement. Alternat. Med. 2013, 432829
16. Jayasundera, K. P.; Kinoshita, H.; Inomata, K. Chem. Lett. 1998, 27, 1227
17. Farran, D.; Parrot, I.; Martinez, J.; Dewynter, G. Angew. Chem., Int. Ed. 2007, 46, 7488
18. Storgaard, M.; Dorwald, F. Z.; Peschke, B.; Tanner, D. J. Org. Chem. 2009, 74, 5032
19. Chaubet, G.; Coursindel, T.; Morelli, X.; Betzi, S.; Roche, P.; Guari, Y.; Lebrun, A.; Toupet, L.; Collette, Y.; Parrot, I.; Martinez, J. Org. Biomol. Chem. 2013, 11, 4719
20. Torres, R. R. The Pauson-Khand Reaction: Scope, Variations and Applications; John Wiley & Sons: U.K., 2012.
21. Park, J. H.; Chang, K.-M.; Chung, Y. K. Coord. Chem. Rev. 2009, 253, 2461
22. Omae, I. Cood. Chem. Rev. 2011, 255, 139
23. Chatani, N. Chem. Rec. 2008, 8, 201
24. Wu, X.-F.; Neumann, H. ChemCatChem 2012, 4, 447
25. Iwata, T.; Inagaki, F.; Mukai, C. Angew. Chem., Int. Ed. 2013, 52, 11138 and references therein
26. Fukuyama, T.; Nakashima, N.; Okada, T.; Ryu, I. J. Am. Chem. Soc. 2013, 135, 1006 and references therein
27. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890
28. Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 4441
29. Ng, S.-S.; Ho, C.-Y.; Schleicher, K. D.; Jamison, T. F. Pure Appl. Chem. 2008, 80, 929
30. Tanaka, K.; Tajima, Y. Eur. J. Org. Chem. 2012, 3715
31. Montgomery, J. Organonickel Chemistry. In Organometallics in Synthesis: Fourth Manual; Lipshutz, B. H., Ed.; Wiley: Hoboken, N.J., 2013; pp 319-428.
32. Ogoshi, S. Yuki Gosei Kagaku Kyokaishi 2013, 71, 14
33. Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299
34. Ogoshi, S.; Ikeda, H.; Kurosawa, H. Angew. Chem., Int. Ed. 2007, 46, 4930
35. Ogoshi, S.; Ikeda, H.; Kurosawa, H. Pure Appl. Chem. 2008, 80, 1115
36. Ohashi, M.; Kishizaki, O.; Ikeda, H.; Ogoshi, S. J. Am. Chem. Soc. 2009, 131, 9160
37. Hoshimoto, Y.; Ohata, T.; Ohashi, M.; Ogoshi, S. Chem.-Eur. J. 2014, 20, 4105
38. Buchwald reported a nickel(0)-catalyzed hetro-Pauson-Khand type reaction of enynes and isocyanides; see
39. Zhang, M.; Buchwald, S. L. J. Org. Chem. 1996, 61, 4498
40. Morimoto, T.; Kakiuchi, K. Angew. Chem., Int. Ed. 2004, 43, 5580
41. Ueda, T.; Konishi, H.; Manabe, K. Org. Lett. 2012, 14, 3100
42. Fujihara, T.; Hosoki, T.; Katafuchi, Y.; Iwai, T.; Terao, J.; Tsuji, Y. Chem. Commun. 2012, 48, 8012
43. Ueda, T.; Konishi, H.; Manabe, K. Org. Lett. 2013, 15, 5370
44. Ueda, T.; Konishi, H.; Manabe, K. Angew. Chem., Int. Ed. 2013, 52, 8611
45. Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T. Justus Liebigs Ann. Chem. 1948, 560, 1
46. Ishizumi, K.; Kojima, A.; Antoku, F.; Saji, I.; Yoshigi, M. Chem. Pharm. Bull. 1995, 43, 2139
47. Matsuki, K.; Inoue, H.; Ishida, A.; Takeda, M.; Nakagawa, M.; Hino, T. Chem. Pharm. Bull. 1994, 42, 9
48. Takebayashi, S.; John, J. M.; Bergens, S. H. J. Am. Chem. Soc. 2010, 132, 12832
49. Yoshida, S.; Igawa, K.; Tomooka, K. J. Am. Chem. Soc. 2012, 134, 19358
50. Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem. 1992, 57, 3760
51. Rassu, G.; Zanardi, F.; Battistini, L.; Gaetani, E.; Casiraghi, G. J. Med. Chem. 1997, 40, 168
52. Zanardi, F.; Battistini, L.; Nespi, M.; Rassu, G.; Spanu, P.; Cornia, M.; Casiraghi, G. Tetrahedron: Asymmetry 1996, 7, 1167
53. Rassu, G.; Pinna, L.; Spanu, P.; Zanardi, F.; Battistini, L.; Casiraghi, G. J. Org. Chem. 1997, 62, 4513
54. Planas, L.; Pérard-Viret, J.; Royer, J. J. Org. Chem. 2004, 69, 3087
55. Curti, C.; Sartori, A.; Battistini, L.; Rassu, G.; Zanardi, F.; Casiraghi, G. Tetrahedron Lett. 2009, 50, 3428