Decarbonylative cycloaddition of phthalic anhydrides with allenes

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1374-1377

  Ochi, Yosuke ^a   Kurahashi, Takuya ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952583005     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200044y     Document Type: Article

References (59)

1. Kajita, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2008, 130, 17226
2. Ooguri, A.; Nakai, K.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 13194
3. For reviews on addition of S-X bond to carbon-carbon unsaturated bonds, see: Han, L.-B.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1999, 395
4. Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435
5. Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A.; Grützmacher, H., Eds.; Wiley-VCH: Zürich, Switzerland, 2001; p 217.
6. Ogawa, A. J. Organomet. Chem. 2000, 611, 463
7. Kondo, T.; Mitudo, T. Chem. Rev. 2000, 100, 3205
8. 2R bond to alkynes, see: Hua, R.; Takeda, H.; Onozawa, S.; Abe, Y.; Tanaka, M. J. Am. Chem. Soc. 2001, 123, 2899
9. For addition of S-C(O)R bond to alkynes, see: Sugoh, K.; Kuniyasu, H.; Sugae, T.; Ohtaka, A.; Takai, Y.; Tanaka, A.; Machino, C.; Kambe, N.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 5108
10. Kuniyasu, H.; Kurosawa, H. Chem.-Eur. J. 2002, 2660
11. Hirai, T.; Kuniyasu, H.; Kambe, N. Chem. Lett. 2004, 33, 1148
12. Hirai, T.; Kuniyasu, H.; Kambe, N. Tetrahedron. Lett. 2005, 46, 117
13. Hirai, T.; Kuniyasu, H.; Terao, J.; Kambe, N. Synlett 2005, 1161
14. Kuniyasu, H.; Yamashita, F.; Hirai, T.; Ye, J.-H.; Fujiwara, S.; Kambe, N. Organometallics 2006, 25, 566
15. Yamashita, F.; Kuniyasu, H.; Terao, J.; Kambe, N. Org. Lett. 2008, 10, 101
16. 2 bond to alkynes, see: Toyofuku, M.; Fujiwara, S.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2005, 127, 9706
17. Kuniyasu, H.; Kato, T.; Asano, S.; Ye, J.-H.; Ohmori, T.; Morita, M.; Hiraike, H.; Fujiwara, S.; Terao, J.; Kurosawa, H.; Kambe, N. Tetrahedron Lett. 2006, 47, 1141
18. For addition of S-CN bond to alkynes, see: Kamiya, I.; Kawakami, J.; Yano, S.; Nomoto, A.; Ogawa, A. Organometallics 2006, 25, 3562
19. For addition of S-allyl bond to alkynes, see: Hua, R.; Takeda, H.; Onozawa, S-y.; Abe, Y.; Tanaka, M. Org. Lett. 2007, 9, 263
20. 2, see: Miura, T.; Yamauchi, M.; Murakami, M. Org. Lett. 2008, 10, 3085
21. Yamauchi, M.; Morimoto, M.; Miura, T.; Murakami, M. J. Am. Chem. Soc. 2010, 132, 54
22. Miura, T.; Yamauchi, M.; Kosaka, A.; Murakami, M. Angew. Chem., Int. Ed. 2010, 49, 4955
23. Miura, T.; Morimoto, M.; Yamauchi, M.; Murakami, M. J. Org. Chem. 2010, 75, 5359
24. 2, see: Shintani, R.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 12356
25. Wang, C.; Tunge, J. A. J. Am. Chem. Soc. 2008, 130, 8118
26. Shintani, R.; Park, S.; Shirozu, F.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 16174
27. Shintani, R.; Park, S.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 14866
28. Shintani, R.; Tsuji, T.; Park, S.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 7508
29. Shintani, R.; Murakami, M.; Hayashi, T. Org. Lett. 2009, 11, 457
30. Shintani, R.; Hayashi, S.; Murakami, M.; Takeda, M.; Hayashi, T. Org. Lett. 2009, 11, 3754
31. The reaction did not proceed in a sealed vessel. Refluxing of reaction solvent is probably essential to promote the exhaust of CO from the reaction system efficiently.
32. Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262
33. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518
34. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345
35. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743
36. Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200
37. Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 2897
38. Miyake, Y.; Nishibayashi, Y.; Uemura, S. Synlett 2008, 1747
39. Kajita, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2008, 130, 6058
40. Fujiwara, K.; Kurahashi, T.; Matsubara, S. Org. Lett. 2010, 12, 4548
41. For oxidative addition of C-N bond to Ni, see: Chan, Y. W.; Renner, M. W.; Balch, A. L. Organometallics 1983, 2, 1888
42. Lin, B. L.; Clough, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 2890
43. Ozerov, O. V.; Guo, C.; Fan, L.; Foxman, B. M. Organometallics 2004, 23, 5573
44. O'Brien, E. M.; Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2003, 125, 10498
45. Johnson, J. B.; Bercot, E. A.; Rowley, J. M.; Coates, G. W.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 2718
46. Yoshino, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 7494
47. Yoshino, Y.; Kurahashi, T.; Matsubara, S. Chem. Lett. 2010, 39, 896
48. Trost, B. M.; Chen, F. Tetrahedron Lett. 1971, 12, 2603
49. Sano, K.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1984, 941
50. Sano, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 2741
51. Yamamoto, T.; Sano, K.; Yamamoto, A. J. Am. Chem. Soc. 1987, 109, 1092
52. Fischer, R.; Walther, D.; Kempe, R.; Sieler, J.; Schönecker, B. J. Organomet. Chem. 1993, 447, 131
53. For migratory insertion of allenes into oxanickelacycles, see: Hoberg, H.; Peres, Y.; Krüger, C.; Tsay, Y.-H. Angew. Chem., Int. Ed. 1987, 26, 771
54. 2Ph catalyst gave racemic cycloadducts 3f (2). This may clearly suggest that the reaction proceeds via π-allylnickel 11, which is a key intermediate for chiral induction.
55. Functionalized δ-lactones are ubiquitous in a variety of biologically active natural products. For recent examples, see: Munro, T. A.; Rizzacasa, M. A.; Roth, B. L.; Toth, B. A.; Yan, F. J. Med. Chem. 2005, 48, 345
56. Nicotra, V. E.; Gil, R. R.; Oberti, J. C.; Burton, G. J. Nat. Prod. 2007, 70, 808
57. Thompson, C. M.; Quinn, C. A.; Hergenrothe, P. J. J. Med. Chem. 2009, 52, 117
58. Meragelman, T. L.; Scudiero, D. A.; Davis, R. E.; Staudt, L. M.; McCloud, T. G.; Cardellina, J. H., II; Shoemaker, R. H. J. Nat. Prod. 2009, 72, 336
59. Haritakun, R.; Sappan, M.; Suvannakad, R.; Tasanathai, K.; Isaka, M. J. Nat. Prod. 2010, 73, 75