Palladium- and ruthenium-catalyzed cycloisomerization of enynamides and enynhydrazides: A rapid approach to diverse azacyclic frameworks

Angewandte Chemie - International Edition

Volumn 52, Issue 35, 2013, Pages 9139-9143

  Walker, P Ross ^a   Campbell, Craig D ^a   Suleman, Abid ^b   Carr, Greg ^b   Anderson, Edward A ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

cyclization; heterocycles; homogeneous catalysis; palladium; ynamide

Indexed keywords

CYCLOISOMERIZATIONS; ELECTRON WITHDRAWING GROUP; EQUIVALENT TRANSFORMATIONS; HETEROCYCLES; HOMOGENEOUS CATALYSIS; MILD REACTION CONDITIONS; STEREO-SELECTIVE; YNAMIDE;

PALLADIUM; REACTION KINETICS; SCAFFOLDS;

CYCLIZATION;

ALKYNE; AMIDE; HETEROCYCLIC COMPOUND; HYDRAZINE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HETEROCYCLES; HOMOGENEOUS CATALYSIS; STEREOISOMERISM; SYNTHESIS; YNAMIDE;

CYCLIZATION; HETEROCYCLES; HOMOGENEOUS CATALYSIS; PALLADIUM; YNAMIDE;

ALKYNES; AMIDES; AZA COMPOUNDS; CATALYSIS; CYCLIZATION; HYDRAZINES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; RUTHENIUM; STEREOISOMERISM;

EID: 84882965240     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304186     Document Type: Article

References (55)

1. A. Marinetti, H. Jullien, A. Voituriez, Chem. Soc. Rev. 2012, 41, 4884
2. S. I. Lee, N. Chatani, Chem. Commun. 2009, 371
3. V. Michelet, P. Y. Toullec, J. P. Genet, Angew. Chem. 2008, 120, 4338
4. Angew. Chem. Int. Ed. 2008, 47, 4268.
5. Platinum-catalyzed:, F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria, Org. Lett. 2004, 6, 1509; Gold-catalyzed
6. S. Couty, C. Meyer, J. Cossy, Angew. Chem. 2006, 118, 6878
7. Angew. Chem. Int. Ed. 2006, 45, 6726; Silver-catalyzed
8. P. Garcia, Y. Harrak, L. Diab, P. Cordier, C. Ollivier, V. Gandon, M. Malacria, L. Fensterbank, C. Aubert, Org. Lett. 2011, 13, 2952
9. For a cyclization of aryl ynamides, see:, Y. Zhang, R. P. Hsung, X. Zhang, J. Huang, B. W. Slafer, A. Davis, Org. Lett. 2005, 7, 1047.
10. N. Saito, Y. Sato, M. Mori, Org. Lett. 2002, 4, 803
11. J. Huang, H. Xiong, R. P. Hsung, C. Rameshkumar, J. A. Mulder, T. P. Grebe, Org. Lett. 2002, 4, 2417
12. H. Wakamatsu, M. Sakagami, M. Hanata, M. Takeshita, M. Mori, Macromol. Symp. 2010, 293, 5.
13. R. L. Greenaway, C. D. Campbell, O. T. Holton, C. A. Russell, E. A. Anderson, Chem. Eur. J. 2011, 17, 14366
14. R. L. Greenaway, C. D. Campbell, H. A. Chapman, E. A. Anderson, Adv. Synth. Catal. 2012, 354, 3187.
15. P. Huang, Z. Y. Chen, Q. Yang, Y. Y. Peng, Org. Lett. 2012, 14, 2790
16. K. A. DeKorver, X.-N. Wang, M. C. Walton, R. P. Hsung, Org. Lett. 2012, 14, 1768
17. D. L. Smith, W. R. F. Goundry, H. W. Lam, Chem. Commun. 2012, 48, 1505
18. R. B. Dateer, B. S. Shaibu, R.-S. Liu, Angew. Chem. 2012, 124, 117
19. Angew. Chem. Int. Ed. 2012, 51, 113
20. P. W. Davies, A. Cremonesi, L. Dumitrescu, Angew. Chem. 2011, 123, 9093
21. Angew. Chem. Int. Ed. 2011, 50, 8931; For recent examples of ynamides in [2+2+2] cyclization, see
22. N. Saito, T. Ichimaru, Y. Sato, Org. Lett. 2012, 14, 1914
23. P. Garcia, Y. Evanno, P. George, M. Sevrin, G. Ricci, M. Malacria, C. Aubert, V. Gandon, Chem. Eur. J. 2012, 18, 4337; For reviews of ynamide chemistry, see
24. Y. Zhang, K. A. DeKorver, H. Y. Li, A. G. Lohse, R. Hayashi, Z. Lu, R. P. Hsung, Chem. Rev. 2010, 110, 5064
25. G. Evano, A. Coste, K. Jouvin, Angew. Chem. 2010, 122, 2902
26. Angew. Chem. Int. Ed. 2010, 49, 2840.
27. For a review of catalytic selective synthesis, see:, J. Mahatthananchai, A. M. Dumas, J. W. Bode, Angew. Chem. 2012, 124, 11114
28. Angew. Chem. Int. Ed. 2012, 51, 10954.
29. B. M. Trost, M. Lautens, Tetrahedron Lett. 1985, 26, 4887
30. B. M. Trost, M. Lautens, J. Am. Chem. Soc. 1985, 107, 1781
31. B. M. Trost, M. Lautens, C. Chan, D. J. Jebaratnam, T. Mueller, J. Am. Chem. Soc. 1991, 113, 636
32. B. M. Trost, G. J. Tanoury, M. Lautens, C. Chan, D. T. Macpherson, J. Am. Chem. Soc. 1994, 116, 4255
33. B. M. Trost, D. L. Romero, F. Rise, J. Am. Chem. Soc. 1994, 116, 4268; For reviews, see
34. B. M. Trost, Chem. Eur. J. 1998, 4, 2405
35. B. M. Trost, Acc. Chem. Res. 1990, 23, 34.
36. J. LePaih, D. C. Rodriguez, S. Derien, P. H. Dixneuf, Synlett 2000, 95
37. M. Mori, Y. Kozawa, M. Nishida, M. Kanamaru, K. Onozuka, M. Takimoto, Org. Lett. 2000, 2, 3245; For a single example of a ruthenium-catalyzed cyclization of an unsubstitued enynamide, requiring an ethene atmosphere, see
38. M. Mori, D. Tanaka, N. Saito, Y. Sato, Organometallics 2008, 27, 6313
39. N. Saito, D. Tanaka, M. Mori, Y. Sato, Chem. Rec. 2011, 11, 186; For ruthenium-catalyzed intermolecular coupling of ynamides with ethene, see
40. N. Saito, K. Saito, M. Shiro, Y. Sato, Org. Lett. 2011, 13, 2718; For a review of ruthenium-catalyzed processes, see
41. B. M. Trost, M. U. Frederiksen, M. T. Rudd, Angew. Chem. 2005, 117, 6788
42. Angew. Chem. Int. Ed. 2005, 44, 6630.
43. N. Saito, Y. Tanaka, Y. Sato, Org. Lett. 2009, 11, 4124
44. A. Fürstner, A. Schlecker, C. W. Lehmann, Chem. Commun. 2007, 4277; For pioneering work with norbornene, see
45. T. Mitsudo, K. Kokuryo, Y. Takegami, J. Chem. Soc. Chem. Commun. 1976, 722; For a Pd-catalyzed formal [2+2] enyne cyclization, see
46. B. M. Trost, M. Yanai, K. Hoogsteen, J. Am. Chem. Soc. 1993, 115, 5294. Although these cyclobutenes could lead to 1,3-dienes by 4π-electrocyclic ring opening, we have found them to be resistant to this process.
47. For a previous example of the contrasting behavior of palladium and ruthenium catalysts in enyne cycloisomerization, see:, B. M. Trost, A. C. Gutierrez, E. M. Ferreira, J. Am. Chem. Soc. 2010, 132, 9206.
48. D. L. Smith, S. R. Chidipudi, W. R. Goundry, H. W. Lam, Org. Lett. 2012, 14, 4934
49. C. Schotes, A. Mezzetti, Angew. Chem. 2011, 123, 3128
50. Angew. Chem. Int. Ed. 2011, 50, 3072
51. H. Y. Li, R. P. Hsung, K. A. DeKorver, Y. G. Wei, Org. Lett. 2010, 12, 3780.
52. B. M. Trost, J. Y. L. Chung, J. Am. Chem. Soc. 1985, 107, 4586.
53. J. P. Michael, Nat. Prod. Rep. 2008, 25, 139.
54. I. R. C. Bick, J. B. Bremner, N. W. Preston, I. C. Calder, J. Chem. Soc. Chem. Commun. 1971, 1155.
55. R. E. Beveridge, R. A. Batey, Org. Lett. 2012, 14, 540.