Regio- and stereoselective synthesis of 2-amino-1,3-diene derivatives by ruthenium-catalyzed coupling of ynamides and ethylene

Organic Letters

Volumn 13, Issue 10, 2011, Pages 2718-2721

  Saito, Nozomi ^a   Saito, Keiichi ^a   Shiro, Motoo ^a,b   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYNE; AMIDE; ETHYLENE; ETHYLENE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; ALKYNES; AMIDES; CATALYSIS; ETHYLENES; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 79956078174     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200812y     Document Type: Article

References (58)

1. For reviews on preparations and reactions of amino-1,3-diene derivatives, see: Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753 and references cited therein
2. Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421 and references cited therein
3. For reviews on the chemistry of ynamides, see: Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575
4. Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379
5. Hsung, R. P., Ed. In Tetrahedron Symposia-in-Print No. 118, Tetrahedron 2006, 62, 3783.
6. Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840
7. DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064
8. For most recent examples of the preparation and reactions of ynamides, see: Gourdet, B.; Lam, H. W. Angew. Chem., Int. Ed. 2010, 49, 8733
9. Sato, A.; Yorimitsu, H.; Oshima, K. Bull. Korean Chem. Soc. 2010, 31, 570
10. Valenta, P.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2010, 132, 14179
11. Poloukhtine, A.; Rassadin, V.; Kuzmin, A.; Popik, V. V. J. Org. Chem. 2010, 75, 5953
12. Jia, W.; Jiao, N. Org. Lett. 2010, 12, 2000
13. Gourdet, B.; Rudkin, M. E.; Lam, H. W. Org. Lett. 2010, 12, 2554
14. Banerjee, B.; Litvinov, D. N.; Kang, J.; Bettale, J. D.; Castle, S. L. Org. Lett. 2010, 12, 2650
15. Kramer, S.; Madsen, J. L. H.; Rottländer, M.; Skrydstrup, T. Org. Lett. 2010, 12, 2758
16. Jouvin, K.; Couty, F.; Evano, G. Org. Lett. 2010, 12, 3272
17. Li, H.; Hsung, R. P.; DeKorver, K. A.; Wei, Y. Org. Lett. 2010, 12, 3780
18. Wakamatsu, H.; Takeshita, M. Synlett 2010, 2322
19. DeKorver, K. A.; North, T. D.; Hsung, R. P. Synlett 2010, 2397
20. Grimster, N. P.; Wilton, D. A. A.; Chan, L. K. M.; Godfrey, C. R. A.; Green, C.; Owen, D. R.; Gaunt, M. J. Tetrahedron 2010, 66, 6429
21. Fadel, A.; Legrand, F.; Evano, G.; Rabasso, N. Adv. Synth. Catal. 2011, 353, 263
22. Schotes, C.; Mezzetti, A. Angew. Chem., Int. Ed. 2011, 50, 3072
23. Davies, P. W.; Cremonesi, A.; Martin, N. Chem. Commun. 2011, 47, 379
24. Mak, X. Y.; Crombie, A. L.; Danheiser, R. J. Org. Chem. 2011, 76, 1852
25. Shindoh, N.; Takemoto, Y.; Takasu, K. Heterocycles 2011, 82, 1133
26. Xu, C.-F.; Xu, M.; Jia, Y.-X.; Li, C.-Y. Org. Lett. 2011, 13, 1556
27. Kramer, S.; Friis, S. D.; Xin, Z.; Odabachian, Y.; Skrydstrup, T. Org. Lett. 2011, 13, 1750. See also: References 2d and 2e
28. For our approach to regio- and stereoselective synthesis of enamide derivatives by Ni(0)-catalyzed multicomponent coupling of ynamide, aldehyde, and silane, see: Saito, N.; Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829
29. Saito, N.; Katayama, T.; Sato, Y. Heterocycles. 2011, 82, 1181
30. For Pd-catalyzed ene-yne coupling, see: Lindhardt, A. T.; Mantel, M. L. H.; Skrydstrup, T. Angew. Chem., Int. Ed. 2008, 47, 2668 For Rh-catalyzed carbozincation of ynamids, see: Gourdet, B.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 3802
31. Gourdet, B.; Rudkin, M. E.; Watts, C. A.; Lam, H. W. J. Org. Chem. 2009, 74, 7849
32. Gourdet, B.; Smith, D. L.; Lam, H. W. Tetrahedron 2010, 66, 6026 For Ti-mediated reductive coupling of ynamide and simple alkyne, see: Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67
33. Hirano, S.; Fukudome, Y.; Tanaka, R.; Sato, F.; Urabe, H. Tetrahedron 2006, 62, 3896
34. For ruthenium-catalyzed ring-closing metathesis of ene-ynamide leading to cyclic-1,3-dienmamide, see: Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803
35. Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417
36. Mori, M.; Wakamatsu, H.; Saito, N.; Sato, Y.; Narita, R.; Sato, Y.; Fujita, R. Tetrahedron 2006, 62, 3872
37. Wakamatsu, H.; Sakagami, M.; Hanata, M.; Takeshita, M.; Mori, M. Macromol. Symp. 2010, 293, 5
38. Trost, B. M. Science 1991, 254, 1471
39. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259
40. For ene-yne coupling via ruthenacyclopentene formation, see: Mitsudo, T.; Zhang, S.-W.; Nagao, M.; Watanabe, Y. Chem. Commun. 1991, 598
41. Trost, B. M.; Martos-Redruejo, A. Org. Lett. 2009, 11, 1071 For ene-yne coupling via hydroruthenation of alkynes, see: Yi, C. S.; Lee, D. W.; Chen, Y. Organometallics 1999, 18, 2043
42. Nishimura, T.; Washitake, Y.; Uemura, S. Adv. Synth. Catal. 2007, 349, 2563 For ene-yne coupling via the formation of ruthenium viynylidene complex, see: Murakami, M.; Ubukata, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 7361 For ene-yne coupling via C-H activation process, see: Kakiuchi, F.; Uetsuhara, T.; Tanaka, Y.; Chatani, N.; Murai, S. J. Mol. Catal. A: Chem. 2002, 182-183, 511
43. Neisius, N. M.; Plietker, B. Angew. Chem., Int. Ed. 2009, 48, 5752 1-Amino-1,3-diene derivatives were synthesized by ruthenium-catalyzed direct cross-coupling of alkynes and N -vinylamides; see: Tsujita, H.; Ura, Y.; Matsuki, S.; Wada, K.; Mitsudo, T.; Kondo, T. Angew. Chem., Int. Ed. 2007, 46, 5160
44. Recently, Tanaka reported the rhodium-catalyzed hydrovinylation-type direct cross-coupling of alkynes and alkenes giving 1,3-dienes via a rhodacyclopentene intermediate; see: Shibata, Y.; Hirano, M.; Tanaka, K. Org. Lett. 2008, 10, 2829
45. Mori, M.; Saito, N.; Tanaka, D.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 5606
46. Mori, M.; Tanaka, D.; Saito, N.; Sato, Y. Organometallics 2008, 27, 6313
47. Tanaka, D.; Sato, Y.; Mori, M. Organometallics 2006, 25, 799
48. Tanaka, D.; Sato, Y.; Mori, M. J. Am. Chem. Soc. 2007, 129, 7730
49. Saito, N.; Tanaka, Y.; Sato, Y. Organometallics 2009, 28, 669
50. Saito, N.; Tanaka, Y.; Sato, Y. Org. Lett. 2009, 11, 4124
51. 6 (5 mol %) in MeCN at room temperature, 2-amino-1,3-diene 6a was produced in 63% yield as a single isomer, and no regioisomer of 6a was observed
52. Recently Hsung reported the synthesis of 2-amino-1,3-diene derivatives via isomerization of allenamide; see: Hayashi, R.; Hsung, R. P.; Feltenberger, J. B.; Lohse, A. G. Org. Lett. 2009, 11, 2125
53. Hayashi, R.; Feltenberger, J. B.; Hsung, R. P. Org. Lett. 2010, 12, 1152
54. For reviews on the use of Oppolzer?s sultam as a chiral auxiliary in asymmetric synthesis, see: Oppolzer, W. Tetrahedron 1987, 43, 1969
55. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241
56. The absolute configuration at the methyne carbon in the cyclohexene ring of 17 was determined by X-ray crystallographic analysis. Crystallographic data of 17 have been deposited at the Cambridge Crystallographic Data Center (CCDC 818816).
57. Pearson, A. J.; Lai, Y.-S.; Srinivasan, K. Aust. J. Chem. 1992, 45, 109
58. Kondo, K.; Matsumoto, M. Tetrahedron Lett. 1976, 17, 4363