Nickel-catalyzed highly regioselective multicomponent coupling of ynamides, aldehydes, and silane: A new access to functionalized enamides

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3829-3832

  Saito, Nozomi ^a   Katayama, Tomoyuki ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; ALKYNE; AMIDE; NICKEL; OXAZOLIDINONE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALDEHYDES; ALKENES; ALKYNES; AMIDES; CATALYSIS; MODELS, MOLECULAR; NICKEL; OXAZOLIDINONES; SILANES;

EID: 55949122495     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801534e     Document Type: Article

References (68)

1. For recent reviews on natural products including enamide structure, see: (a) Yet, L. Chem. Rev. 2003, 103, 4283.
2. (b) Joullié, M. M.; Richard, D. J. Chem. Commun. 2004, 2011.
3. (c) Tan, N.-H.; Zhu, J. Chem. Rev. 2006, 106, 840.
4. For reviews on asymmetric hydrogenation, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH, Inc.; New York, 2000; pp 1-110.
5. (b) Kitamura, M.; Noyori, R. In Ruthenium in Organic Synthesis; Murahashi, S.-i., Ed.; Wiley-VCH, Inc.: New York, 2002; pp 3-52.
6. (c) Chi, Y.; Tang, W.; Zhang, X. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2004; pp 1-31.
7. (a) Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139.
8. (b) Arisawa, M.; Terada, Y.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2002, 41, 4732.
9. (c) Krompiec, S.; Pigulla, M.; Krompiec, M.; Baj, S.; Mrowiec-Bialon, J.; Kasperczyk, J. Tetrahedron Lett. 2004, 5257, and references cited therein.
10. (a) Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413.
11. (b) Goossen, L. J.; Rauhaus, J. E.; Deng, G. Angew. Chem., Int. Ed. 1995, 44, 4042.
12. (c) Yudha S., S.; Kuninobu, Y.; Takai, K. Org. Lett. 2007, 9, 5609.
13. For a review, see: Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973, and referencescited therein.
14. Bolshan, Y.; Batey, R. A. Angew. Chem., Int. Ed. 2008, 47, 2019.
15. (a) Hosokawa, T.; Takano, M.; Kuroki. Y.; Murahashi, S.-i. Tetrahedron Lett. 1992, 33, 6643.
16. (b) Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2003, 125, 12996.
17. (c) Brice, J. L.; Harang, J. E.; Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 2868.
18. Tsujita, K.; Ura, Y.; Matsuki, S.; Wada, K.; Mitsudo, T.; Kondo, T. Angew. Chem., Int. Ed. 2007, 46, 5160.
19. For recent reviews on chemistry of ynamine and ynamide, see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
20. (b) Hsung, R. P., Ed. In Tetrahedron Symposia-in-Print No. 118. Tetrahedron 2006, 62, 3783.
21. Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170.
22. (a) Hoffmann, R. W.; Bruckner, D. New J. Chem. 2001, 25, 369.
23. (b) Timbart, L.; Cintrat, J.-C. Chem. Eur. J. 2002, 8, 1637.
24. (c) Chechik-Lankin, H.; Livshin, S.; Marek, I. Synlett 2005, 2098.
25. (d) Buissonneaud, D.; Cintrat, J.-C. Tetrahedron Lett. 2006, 47, 3139.
26. (a) Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681.
27. (b) Villeneuve, K.; Riddell, N.; Tam, W. Tetrahedron 2006, 62, 3823.
28. (a) Zhu, J.; Bienaymé, H., Eds. In Multicomponent Reactions; Wiley-VCH Verlag Gmbh and Co. KGaA: Weinheim, Germany, 2005.
29. (b) Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602.
30. (a) Takimoto, M.; Hiraga, Y.; Sato, Y.; Mori, M. Tetrahedron Lett. 1998, 39, 4543.
31. (b) Sato, Y.; Sawaki, R.; Mori, M. Organometallics 2001, 20, 5510.
32. (c) Sawaki, R.; Sato, Y.; Mori, M. Org. Lett. 2004, 6, 1131.
33. (d) Sato, Y.; Hinata, Y.; Seki, R.; Oonishi, Y.; Saito, N. Org. Lett. 2007, 9, 5597.
34. 2Al(acac), see: (e) Sato, Y.; Sawaki, R.; Saito, N.; Mori, M. J. Org. Chem. 2002, 67, 656.
35. 3 instead of silane, see: (f) Sato, Y.; Saito, N.; Mori, M. Chem. Lett. 2002, 18.
36. (g) Saito, N.; Mori, M.; Sato, Y. J. Organomet. Chem. 2007, 692, 460.
37. For reviews on Ni(0)-catalyzed multicomponent coupling, see: (a) Ikeda, S.-i. Acc. Chem. Res. 2000, 33, 511.
38. (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
39. (c) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890, and references cited therein.
40. For recent examples of Ni(0)-catalyzed multicomponent coupling, see: (a) Terao, J.; Nu, S.; Chowdhury, F. A.; Nakamura, A.; Kambe, N. Adv. Synrh. Catal. 2004, 346, 905.
41. (b) Kimura, M.; Miyachi, A.; Kojima, K.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2004, 126, 14360.
42. (c) Shirakawa, E.; Yamamoto, Y.; Nakao, Y.; Oda, S.; Tsuchimoto, T.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 3448.
43. (d) Kimura, M.; Ezoe, A.; Mori, M.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 201.
44. (e) Kimura, M.; Kojima, K.; Tatsuyama, Y.; Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 6332.
45. (f) Cozzi, P. G.; Rivalta, E. Angew. Chem., Int. Ed. 2005, 44, 3600.
46. (g) Ng, S.-S.; Ho, C.-Y.; Jamison, T. F. J. Am. Chem. Soc. 2006, 128, 11513.
47. (h) Ho, C.-Y.; Jamison, T. F. Angew. Chem., Int. Ed. 2007, 46, 782.
48. (i) Chrovian, C. C.; Montgomery, J. Org. Lett. 2007, 9, 537.
49. (j) Jayanth, T. T.; Cheng, C.-H. Angew. Chem., Int. Ed. 2007, 46, 5921.
50. (k) Herath, A.; Li, W.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 469.
51. For Ni-catalyzed three-component coupling of alkynes, which have alkyl, aryl, or silyl groups on the sp-hybridized carbon atom, aldehydes, and silanes by Montgomery, see: (a) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
52. (b) Sa-ei, K.; Montgomery, J. Org. Lett. 2006, 8, 4441.
53. (c) Chaulagain, M. R.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc. 2007, 129, 9568.
54. For other examples of Ni-catalyzed reductive alkyne-aldehyde coupling, see: (d) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 179, 9065.
55. (e) Huang, W.-S.; Chan, J.; Jamison, T. F. Org. Lett. 2000, 2, 4221.
56. (f) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3422.
57. (g) Luanphaisarnnont, T.; Ndubaku, C. O.; Jamison, T. F. Org. Lett. 2005, 7, 2937.
58. For a Ti-mediated reductive coupling of ynamides and aldehydes, see: Tanaka, R; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67.
59. For recent examples of the preparation of γ-alkoxy enamide derivatives and their synthetic application, see: (a) McAlonan, H.; Murphy, J. P.; Nieuwenhuyzen, M.; Reynolds, K.; Sarma, P. K. S.; Stevenson, P. J.; Thompson, N. J. Chem. Soc., Perkin Trans. 1 2002, 69.
60. (b) Ylioja, P. M.; Mosley, A. D.; Chariot, C. E.; Carbery, D. R. Tetrahedron Lett. 2008, 49, 1111.
61. In this work, the ynamides were synthesized by Hsung's Cu-catalyzed coupling reaction of haloalkynes and amides. Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
62. Olefinic geometry was determined by an NOE experiment. See the Supporting Information.
63. For a hydrosilylation of alkyne with Ni-NHC catalyst, see: Chaulagain, M. R.; Mahandru, G. M.; Montgomery, J. Tetrahedron 2006, 62, 7560.
64. 2-arylaldehydenickel complexes from zerovalent nickel complex and aldehyde, see: (a) Walther, D. J. Organomet. Chem. 1980, 190, 393.
65. (b) Ogoshi, S.; Kamada, H.; Kurosawa, H. Tetrahedron 2006, 62, 7583.
66. Recently, oxanickelacyclopentene from zerovalent nickel, aldehyde, and alkyne was isolated and its structure was elucidated by X-ray analysis, see: Ogoshi, S.; Arai, T.; Ohashi, M.; Kurosawa, H. Chem. Commun. 2008, 1347.
67. Montgomery suggested the reaction mechanism via oxanickel-acyclopentene formation followed by σ-bond metathesis with silane in his three-component coupling of alkynes, aldehydes, and silanes using Ni-NHC catalyst. See refs 17a and 17c.
68. Similar regioselectivity has been observed in Lewis acid-mediated coupling of ynamides and aldehydes or ketones demonstrated by Hsung. see: You, L.; Al-Rashid, Z. F.; Figueroa, R.; Ghosh, S. K.; Li. G., Lu, T.; Hsung, R. P. Synlett 2007, 1656.