Regioselective synthesis of enones via a titanium-promoted coupling of unsymmetrical alkynes with Weinreb amides

Journal of Organic Chemistry

Volumn 79, Issue 17, 2014, Pages 8469-8476

  Silwal, Sajan ^a   Rahaim, Ronald J ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; HYDROCARBONS; STEEL BEAMS AND GIRDERS; SYNTHESIS (CHEMICAL); TITANIUM;

CHEMO-SELECTIVITY; COUPLING REACTION; REGIOSELECTIVE SYNTHESIS; ROOM TEMPERATURE; UNSYMMETRICAL INTERNAL ALKYNES; WEINREB AMIDES;

REGIOSELECTIVITY;

ALKYNE; AMIDE; ENONE DERIVATIVE; KETONE DERIVATIVE; TITANIUM; UNCLASSIFIED DRUG;

ACYLATION; ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOPROPANATION; DEHYDROGENATION; GAS CHROMATOGRAPHY; ISOMERIZATION; MASS SPECTROMETRY; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKYNES; AMIDES; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM; TITANIUM;

EID: 84920844284     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5014417     Document Type: Article

References (56)

1. Ueda, A.; Yamamoto, A.; Kato, D.; Kishi, Y. J. Am. Chem. Soc. 2014, 136, 5171-5176
2. Ding, C.; Zhang, Y.; Chen, H.; Yang, Z.; Wild, C.; Ye, N.; Ester, C. D.; Xiong, A.; White, M. A.; Shen, Q.; Zhou, J. J. Med. Chem. 2013, 56, 8814-8825
3. Marsden, S. P. Sci. Synth. 2005, 26, 1045-1121
4. Buckle, D. R.; Pinto, I. L. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 7, pp 119-149.
5. Larock, R. C. Comprehensive Organic Transformations, 2 nd ed.; John Wiley & Sons: New York, 1999; pp 251-256.
6. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 2, pp 133-179.
7. Ren, K.; Hu, B.; Zhao, M.; Tu, Y.; Xie, X.; Zhang, Z. J. Org. Chem. 2014, 79, 2170-2177
8. Nakano, T.; Ishii, Y.; Ogawa, M. J. Org. Chem. 1987, 52, 4855-4859
9. Liu, J.; Ma, S. Org. Lett. 2013, 15, 5150-5153
10. Catino, A. J.; Forslund, R. E.; Doyle, M. P. J. Am. Chem. Soc. 2004, 126, 13622-13623
11. Nicolaou, K. C.; Zhong, Y. L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596-7597
12. Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675-5677
13. Muzart, J. Eur. J. Org. Chem. 2010, 3779-3790
14. Pennell, M. N.; Unthank, M. G.; Turner, P.; Sheppard, T. D. J. Org. Chem. 2011, 76, 1479-1482
15. Sugawara, Y.; Yamada, W.; Yoshida, S.; Ikeno, T.; Yamada, T. J. Am. Chem. Soc. 2007, 129, 12902-12903
16. Cadierno, V.; Crochet, P.; Garcia-Garrido, S. E.; Gimeno, J. Dalton Trans. 2010, 39, 4015-4031
17. Collins, B. S. L.; Suero, M. G.; Gaunt, M. J. Angew. Chem., Int. Ed. 2013, 52, 5799-5802
18. Xiong, Y.-P.; Wu, M.-Y.; Zhang, X.-Y.; Ma, C.-L.; Huang, L.; Zhao, L.-J.; Tan, B.; Liu, X.-Y. Org. Lett. 2014, 16, 1000-1003
19. For a review of transition-metal-catalyzed hydroacylation, see: Willis, M. C. Chem. Rev. 2010, 110, 725-748
20. Biju, A. T.; Wurz, N. E.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 5970-5971
21. Parsons, S. R.; Hooper, J. F.; Willis, M. C. Org. Lett. 2011, 13, 998-1000
22. Kong, K.; Moussa, Z.; Lee, C.; Romo, D. J. Am. Chem. Soc. 2011, 133, 19844-19856
23. Fu, R.; Ye, J.-L.; Dai, X.-J.; Ruan, Y.-P.; Huang, P.-Q. J. Org. Chem. 2010, 75, 4230-4243
24. Fleming, I.; Pearce, A. J. Chem. Soc., Perkin Trans. 1 1980, 2485-2489
25. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557-1565
26. Ishiyama, N.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1991, 64, 1999-2001
27. Wolan, A.; Six, Y. Tetrahedron 2010, 66, 15-61
28. Wolan, A.; Six, Y. Tetrahedron 2010, 66, 3097-3133
29. Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834
30. Kasatkin, A.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1995, 36, 6075-6078
31. Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216
32. Six, Y. Eur. J. Org. Chem. 2003, 1157-1171
33. Wolan, A.; Cadoret, F.; Six, Y. Tetrahedron 2009, 65, 7429-7439
34. Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228-3229
35. Yamashita, K.; Chatani, N. Synlett 2005, 919-922
36. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818
37. Balasubramaniam, S.; Aidhen, I. S. Synthesis 2008, 3707-3738
38. Bach, J.; Galobardes, M.; Garcia, J.; Romea, P.; Tey, C.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 6765-6768
39. Yu, L.-F.; Hu, H.-N.; Nan, F.-J. J. Org. Chem. 2011, 76, 1448-1451
40. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206
41. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886
42. Rassadin, V.; Six, Y. Tetrahedron 2014, 70, 787-794
43. Obora, Y.; Moriya, H.; Tokunaga, M.; Tsuji, Y. Chem. Commun. 2003, 2820-2821
44. Eisch, J. J.; Gitua, J. N. Organometallics 2003, 22, 24-26
45. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapauntzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320
46. For a similar trend in the reaction of aromatic Weinreb amides, see: Rudzinski, D. M.; Kelly, C. B.; Leadbeater, N. E. Chem. Commun. 2012, 48, 9610-9612
47. For an example of a pyridine ligand on a titanium complex, see: Noor, A.; Kempe, R. Eur. J. Inorg. Chem. 2008, 2377-2381
48. Spencer, W. T., III; Vaidya, T.; Frontier, A. J. Eur. J. Org. Chem. 2013, 3621-3633
49. Suzuki, D.; Nobe, Y.; Watai, Y.; Tanaka, R.; Takayama, Y.; Sato, F.; Urabe, H. J. Am. Chem. Soc. 2005, 127, 7474-7479
50. Teng, X.; Wada, T.; Okamoto, S.; Sato, F. Tetrahedron Lett. 2001, 42, 5501-5503
51. Rudzinski, D. M.; Kelly, C. B.; Leadbeater, N. E. Chem. Commun. 2012, 48, 9610-9612
52. Shintani, R.; Kimura, T.; Hayashi, T. Chem. Commun. 2005, 3213-3214
53. Niu, T.; Zhang, W.; Huang, D.; Xu, C.; Wang, H.; Hu, Y. Org. Lett. 2009, 11, 4474-4477
54. Wei, Y.; Tang, J.; Cong, X.; Zeng, X. Green Chem. 2013, 15, 3165-3169
55. Fujihara, T.; Tatsumi, K.; Terao, J.; Tsuji, Y. Org. Lett. 2013, 15, 2286-2289
56. Ooi, I.; Sakurai, T.; Takaya, J.; Iwasawa, N. Chem.-Eur. J. 2012, 18, 14618-14621