Ruthenium-catalyzed alkene-alkyne coupling of disubstituted olefins: Application to the stereoselective synthesis of trisubstituted enecarbamates

Journal of the American Chemical Society

Volumn 137, Issue 2, 2015, Pages 620-623

  Trost, Barry M ^a   Cregg, James J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; HYDROCARBONS; OLEFINS; STEREOCHEMISTRY; STEREOSELECTIVITY;

1 ,2-AMINO ALCOHOLS; ALKYNE COUPLING; ASYMMETRIC SYNTHESIS; COMPLEX MOLECULES; DIRECTING GROUPS; STEREOSELECTIVE SYNTHESIS;

SYNTHESIS (CHEMICAL);

ALKENE; ALKYNE; AMINOALCOHOL; CARBAMIC ACID DERIVATIVE; RUTHENIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; STEREOCHEMISTRY;

EID: 84921506049     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja511911b     Document Type: Article

References (55)

1. Trost, B. M.; Pinkerton, A. B.; Toste, F. D.; Sperrle, M. J. Am. Chem. Soc. 2001, 123, 12504
2. Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468
3. Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067
4. Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630
5. Trost, B. M.; Machacek, M. R.; Faulk, B. D. J. Am. Chem. Soc. 2006, 128, 6745
6. Trost, B. M.; Wrobleski, S. T.; Chisholm, J. D.; Harrington, P. E.; Jung, M. J. Am. Chem. Soc. 2005, 127, 13589
7. Trost, B. M.; Papillon, J. P. N.; Nussbaumer, T. J. Am. Chem. Soc. 2005, 127, 17921
8. Trost, B. M.; Gunzner, J. L.; Dirat, O.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 10396
9. Trost, B. M.; Stivala, C. E.; Hull, K. L.; Huang, A.; Fandrick, D. R. J. Am. Chem. Soc. 2014, 136, 88
10. Trost, B. M.; Dong, G. Nature 2008, 456, 485
11. Three examples of cyclic disubstituted olefins have been reported. However extension of these substrates has been unsuccessful; see: Trost, B. M.; Dean Toste, F. Tetrahedron Lett. 1999, 40, 7739
12. Gopalaiah, K.; Kagan, H. B. Chem. Rev. 2011, 111, 4599
13. Gourdet, B.; Lam, H. W. Angew. Chem., Int. Ed. 2010, 49, 8733
14. Phipps, R. J.; Hiramatsu, K.; Toste, F. D. J. Am. Chem. Soc. 2012, 134, 8376
15. Song, Z.; Lu, T.; Hsung, R. P.; Al-Rashid, Z. F.; Ko, C.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 4069
16. Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 7993
17. Lu, M.; Lu, Y.; Zhu, D.; Zeng, X.; Li, X.; Zhong, G. Angew. Chem., Int. Ed. 2010, 49, 8588
18. Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 7843
19. Kobayashi, S.; Gustafsson, T.; Shimizu, Y.; Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8, 4923
20. Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292
21. Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2008, 130, 14452
22. Matsubara, R.; Kobayashi, S. Acc. Chem. Res. 2008, 41, 292
23. Terada, M.; Soga, K.; Momiyama, N. Angew. Chem., Int. Ed. 2008, 47, 4122
24. Klaus, S.; Neumann, H.; Jacobi von Wangelin, A.; Goerdes, D.; Struebing, D.; Huebner, S.; Hateley, M.; Weckbecker, C.; Huthmacher, K.; Riermeier, T.; Beller, M. J. Organomet. Chem. 2004, 689, 3685
25. Yet, L. Chem. Rev. 2003, 103, 4283
26. Shen, R.; Lin, C. T.; Bowman, E. J.; Bowman, B. J.; Porco, J. A. J. Am. Chem. Soc. 2003, 125, 7889
27. Pandey, A. K.; Sharma, R.; Shivahare, R.; Arora, A.; Rastogi, N.; Gupta, S.; Chauhan, P. M. S. J. Org. Chem. 2013, 78, 1534
28. Gourdet, B.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 3802
29. Gourdet, B.; Rudkin, M. E.; Watts, C. A.; Lam, H. W. J. Org. Chem. 2009, 74, 7849
30. Gourdet, B.; Smith, D. L.; Lam, H. W. Tetrahedron 2010, 66, 6026
31. Wallace, D. J.; Klauber, D. J.; Chen, C.; Volante, R. P. Org. Lett. 2003, 5, 4749
32. Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809
33. Bolshan, Y.; Batey, R. A. Angew. Chem. 2008, 120, 2139
34. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338
35. Trost, B. M.; Mueller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888
36. Trost, B. M.; Machacek, M. R.; Ball, Z. T. Org. Lett. 2003, 5, 1895
37. Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2011, 133, 9164
38. Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1998, 63, 8983
39. Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070
40. Komeyama, K.; Morimoto, T.; Takaki, K. Angew. Chem., Int. Ed. 2006, 45, 2938
41. Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 6042
42. Buzas, A.; Gagosz, F. J. Am. Chem. Soc. 2006, 128, 12614
43. Cochran, B. M.; Michael, F. E. J. Am. Chem. Soc. 2008, 130, 2786
44. Liu, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 1570
45. Ohmiya, H.; Moriya, T.; Sawamura, M. Org. Lett. 2009, 11, 2145
46. Hesp, K. D.; Tobisch, S.; Stradiotto, M. J. Am. Chem. Soc. 2010, 132, 413
47. Murtagh, L.; Dunne, C.; Gabellone, G.; Panesar, N. J.; Field, S.; Reeder, L. M.; Saenz, J.; Smith, G. P.; Kissick, K.; Martinez, C.; Van Alsten, J. G.; Evans, M. C.; Franklin, L. C.; Nanninga, T. N.; Wong, J. Org. Process Res. Dev. 2011, 15, 1315
48. Bergmeier, S. C. Tetrahedron 2000, 56, 2561
49. Kang, T.; Kim, H.; Kim, J. G.; Chang, S. Chem. Commun. 2014, 50, 12073
50. Karjalainen, O. K.; Koskinen, A. M. P. Org. Biomol. Chem. 2012, 10, 4311
51. Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338
52. Trost, B. M.; Miege, F. J. Am. Chem. Soc. 2014, 136, 3016
53. Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779
54. Boyce, G. R.; Johnson, J. S. Angew. Chem., Int. Ed. Engl. 2010, 49, 8930
55. Sharpe, R. J.; Malinowski, J. T.; Johnson, J. S. J. Am. Chem. Soc. 2013, 135, 17990