Divergent synthesis of functionalized carbocycles through organosilane-directed asymmetric alkyne-alkene reductive coupling and annulation sequence

Journal of the American Chemical Society

Volumn 134, Issue 44, 2012, Pages 18440-18446

  Wu, Jie ^a   Pu, Yi ^a   Panek, James S ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLSILANES; CARBOCYCLES; CARBOCYCLIC RINGS; DIVERGENT SYNTHESIS; FUNCTIONALIZED; HOMODIMERIZATION; REDUCTIVE COUPLINGS;

OLEFINS;

ACETYLENE;

ALKENE; ALKYNE; HOMODIMER; SILANE DERIVATIVE; TITANIUM;

ALLYLATION; ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; DIMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; ALKYNES; ALLYL COMPOUNDS; CYCLIZATION; DIMERIZATION; HYDROCARBONS, CYCLIC; OXIDATION-REDUCTION; SILANES; STEREOISOMERISM;

EID: 84868591731     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3083945     Document Type: Article

References (57)

1. Barbero, A.; Pulido, F. J. Acc. Chem. Res. 2004, 37, 817
2. Chabaud, L.; James, P.; Landais, Y. Eur. J. Org. Chem. 2004, 3173
3. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063
4. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293
5. Saito, N.; Kobayashi, A.; Sato, Y. Angew. Chem., Int. Ed. 2012, 51, 1228
6. Selander, N.; Paasch, J. R.; Szabó, K. J. J. Am. Chem. Soc. 2011, 133, 409
7. Wu, J.; Chen, Y.; Panek, J. S. Org. Lett. 2010, 12, 2112
8. Kacprzynski, M. A.; May, T. L.; Kazane, S. A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 4554
9. Shintani, R.; Ichikawa, Y.; Hayashi, T.; Chen, J.; Nakao, Y.; Hiyama, T. Org. Lett. 2007, 9, 4643
10. Suginome, M.; Ito, Y. J. Organomet. Chem. 2003, 685, 218
11. Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920
12. Davies, H. M.; Hansen, T.; Rutberg, J.; Bruzinski, P. R. Tetrahedron Lett. 1997, 38, 1741
13. Reichard, H. A.; Micalizio, G. C. Angew. Chem., Int. Ed. 2007, 46, 1440
14. Gonzalez, A. Z.; Soderquist, J. A. Org. Lett. 2007, 9, 1081
15. Betson, M. S.; Fleming, I. Org. Biomol. Chem. 2003, 1, 4005
16. Reichard, H. A.; Micalizio, G. C. Chem. Sci. 2011, 2, 573
17. Reichard, H. A.; Mclaughlin, M.; Chen, M. Z.; Micalizio, G. C. Eur. J. Org. Chem. 2010, 391
18. Jeganmohan, M.; Cheng, C.-H. Chem.-Eur. J. 2008, 14, 10876
19. Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 43, 4441
20. Broene, R. D. Top. Curr. Chem. 2007, 279, 209
21. Gibson, S. E.; Mainolfi, N. Angew. Chem., Int. Ed. 2005, 44, 3022
22. Li, W.; Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2009, 131, 17024
23. Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 8132
24. Chang, H.-T.; Jayanth, T. T.; Wang, C.-C.; Cheng, C.-H. J. Am. Chem. Soc. 2007, 129, 12032
25. Aoki, K.; Peat, A. J.; Buchwald, S. J. J. Am. Chem. Soc. 1998, 120, 3068
26. Wei, C.-H.; Mannathan, S.; Cheng, C.-H. J. Am. Chem. Soc. 2011, 133, 6942
27. Canterbury, D. P.; Micalizio, G. C. J. Am. Chem. Soc. 2010, 132, 7602
28. Kolundzic, F.; Micalizio, G. C. J. Am. Chem. Soc. 2007, 129, 15112
29. For allylic 1,3-strain, see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841
30. Chalifoux, W. A.; Reznik, S. K.; Leighton, J. L. Nature 2012, 487, 86
31. Wu, J.; Zhu, K.; Yuan, P.; Panek, J. S. Org. Lett. 2012, 14, 3624
32. Wu, J.; Becerril, J.; Lian, Y.; Davies, H. M. L.; Porco, J. A.; Panek, J. S. Angew. Chem., Int. Ed. 2011, 50, 5938
33. Lee, J.; Panek, J. S. Org. Lett. 2011, 13, 502
34. Brawn, R. A.; Panek, J. S. Org. Lett. 2010, 12, 4624
35. Huber, J. D.; Leighton, J. L. J. Am. Chem. Soc. 2007, 129, 14552
36. Tinsley, J. M.; Mertz, E.; Chong, P. Y.; Rarig, R. F.; Roush, W. R. Org. Lett. 2005, 7, 4245
37. Mertz, E.; Tinsley, J. M.; Roush, W. R. J. Org. Chem. 2005, 70, 8035
38. Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488
39. Roush, W. R.; Madar, D. J.; Coffey, D. S. Synlett 2001, 955
40. Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094
41. For details concerning the preparation of propargylsilanes 1, see Supporting Information. Also see: Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 3231
42. Hamada, T.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1999, 121, 7342
43. For discussion of the alkyne-titanium complex, see: Perez, L. J.; Shimp, H. L.; Micalizio, G. C. J. Org. Chem. 2009, 74, 7211
44. A single example of titanium-mediated coupling using an α-chiral alkyne (methyl-substituted) with an achiral monosubstituted alkene has been reported in Micalizio's synthesis of dictyostatin with low regioselectivity; see the supporting information of Shimp, H. L.; Micalizio, G. C. Tetrahedron 2009, 65, 5908
45. Judd, W. R.; Ban, S.; Aube, J. J. Am. Chem. Soc. 2006, 128, 13736
46. Masse, C. E.; Dakin, L. A.; Knight, B. S.; Panek, J. S. J. Org. Chem. 1997, 62, 9335
47. Lin, M.; Kang, G.; Guo, Y.; Yu, Z. J. Am. Chem. Soc. 2012, 134, 398
48. Aikawa, K.; Okamoto, T.; Mikami, K. J. Am. Chem. Soc. 2012, 134, 10329
49. Jung, B.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 1490
50. Chen, Z.; Duan, X.; Zhou, P.; Ali, S.; Luo, J.; Liang, Y. Angew. Chem., Int. Ed. 2012, 51, 1370
51. Tan, B.; Candeias, N. R.; Barbas, C. F. Nature Chem 2011, 3, 473
52. For mono-oxidation using iodobenzenediacetate and TEMPO, see: Yadav, J. S.; Rajender, V.; Gangadhara Rao, Y. Org. Lett. 2010, 12, 348
53. Miura, K.; Hondo, T.; Okajima, S.; Nakagawa, T.; Takahashi, T.; Hosomi, A. J. Org. Chem. 2002, 67, 6082
54. For TBAF-DMF-mediated desilylation, see: Heitzman, C. L.; Lambert, W. T.; Mertz, E.; Shotwell, J. B.; Tinsley, J. M.; Va, P.; Roush, W. R. Org. Lett. 2005, 7, 2405
55. Qiao, M.; Ji, N.; Liu, X.; Li, K.; Zhu, Q.; Xue, Q. Bioorg. Med. Chem. Lett. 2010, 20, 5677
56. Kim, H.; Baker, J. B.; Lee, S.; Park, Y.; Bolduc, K. L.; Park, H.; Dickens, M. G.; Lee, D.; Kim, Y.; Hong, J. J. Am. Chem. Soc. 2009, 131, 3192
57. For a recent example of Sakurai dimerization, see: Gesinski, M. G.; Rychnovsky, S. D. J. Am. Chem. Soc. 2011, 133, 9727-9729