Regio- and enantioselective cobalt-catalyzed reductive [3+2] cycloaddition reaction of alkynes with cyclic enones: A route to bicyclic tertiary alcohols

Angewandte Chemie - International Edition

Volumn 51, Issue 42, 2012, Pages 10592-10595

  Wei, Chu Hung ^a   Mannathan, Subramaniyan ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

alkynes; cobalt; cobaltacyclopentene; cycloaddition; tertiary alcohols

Indexed keywords

EID: 84867544024     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201205115     Document Type: Article

References (59)

1. M. Juhl, D. Tanner, Chem. Soc. Rev. 2009, 38, 2983
2. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742
3. Angew. Chem. Int. Ed. 2002, 41, 1668.
4. K. P. C. Vollhardt, Angew. Chem. 1984, 96, 525
5. Angew. Chem. Int. Ed. Engl. 1984, 23, 539
6. S. Saito, Y. Yamamoto, Chem. Rev. 2000, 100, 2901
7. L. Yet, Chem. Rev. 2000, 100, 2963
8. J. A. Varela, C. Saá, Chem. Rev. 2003, 103, 3787
9. M. P. Croatt, P. A. Wender, Eur. J. Org. Chem. 2010, 19
10. I. Omae, Appl. Organomet. Chem. 2008, 22, 149.
11. M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49
12. H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151
13. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117
14. Z.-X. Yu, Y. Wang, Y. Wang, Chem. Asian J. 2010, 5, 1072.
15. K. Suzuki, H. Urabe, F. Sato, J. Am. Chem. Soc. 1996, 118, 8729
16. H. Urabe, K. Suzuki, F. Sato, J. Am. Chem. Soc. 1997, 119, 10014.
17. S. K. Chowdhury, K. K. D. Amarasinghe, M. J. Heeg, J. Montgomery, J. Am. Chem. Soc. 2000, 122, 6775
18. G. M. Mahandru, A. R. L. Skauge, S. K. Chowdhury, K. K. D. Amarasinghe, M. J. Heeg, J. Montgomery, J. Am. Chem. Soc. 2003, 125, 13481.
19. A. Herath, J. Montgomery, J. Am. Chem. Soc. 2006, 128, 14030
20. A. D. Jenkins, A. Hearth, M. Song, J. Montgomery, J. Am. Chem. Soc. 2011, 133, 14460; for related nickel-catalyzed reductive coupling of alkynes and enones, see
21. A. Herath, B. B. Thompson, J. Montgomery, J. Am. Chem. Soc. 2007, 129, 8712
22. W. Li, A. Herath, J. Montgomery, J. Am. Chem. Soc. 2009, 131, 17024
23. J. Montgomery, K. K. D. Amarasinghe, S. K. Chowdhury, E. Oblinger, J. Seo, A. V. Savchenko, Pure Appl. Chem. 2002, 74, 129
24. A. Herath, J. Montgomery, J. Am. Chem. Soc. 2008, 130, 8132
25. A. Herath, W. Li, J. Montgomery, J. Am. Chem. Soc. 2008, 130, 469.
26. H.-T. Chang, T. T. Jayanth, C.-H. Cheng, J. Am. Chem. Soc. 2007, 129, 4166
27. K. C. Chao, D. K. Rayabarapu, C.-C. Wang, C.-H. Cheng, J. Org. Chem. 2001, 66, 8804.
28. T. Hata, N. Hirone, S. Sujaku, K. Nakano, H. Urabe, Org. Lett. 2008, 10, 5031.
29. M. Ohoshi, T. Taniguchi, S. Ogoshi, J. Am. Chem. Soc. 2011, 133, 14900.
30. C.-C. Wang, P.-S. Lin, C.-H. Cheng, J. Am. Chem. Soc. 2002, 124, 9696
31. H.-T. Chang, T. T. Jayanth, C.-C. Wang, C.-H. Cheng, J. Am. Chem. Soc. 2007, 129, 12032
32. D. K. Rayabarapu, C.-H. Cheng, Chem. Eur. J. 2003, 9, 3164
33. C.-H. Yeh, R. P. Korivi, C.-H. Cheng, Angew. Chem. 2008, 120, 4970
34. Angew. Chem. Int. Ed. 2008, 47, 4892
35. Y.-C. Wong, K. Parthasarathy, C.-H. Cheng, J. Am. Chem. Soc. 2009, 131, 18252
36. S. Mannathan, C.-H. Cheng, Chem. Eur. J. 2012, 18, 11771.
37. T. Sambaiah, L.-P. Li, D.-J. Huang, C.-H. Lin, D. K. Rayabarapu, C.-H. Cheng, J. Org. Chem. 1999, 64, 3663
38. M. Shanmugasundaram, M.-S. Wu, C.-H. Cheng, Org. Lett. 2001, 3, 4233.
39. M. Movassaghi, B. Chen, Angew. Chem. 2007, 119, 571
40. Angew. Chem. Int. Ed. 2007, 46, 565.
41. J. Karthikeyan, M. Jeganmohan, C.-H. Cheng, Chem. Eur. J. 2010, 16, 8989.
42. B. M. Trost, Science 1991, 254, 1471
43. B. M. Trost, Angew. Chem. 1995, 107, 285
44. Angew. Chem. Int. Ed. Engl. 1995, 34, 259
45. B. M. Trost, Acc. Chem. Res. 2002, 35, 695.
46. W. Zi, S. Yu, D. Ma, Angew. Chem. 2010, 122, 6023
47. Angew. Chem. Int. Ed. 2010, 49, 5887
48. S. Xing, Y. Li, Z. Li, C. Liu, J. Ren, Z. Wang, Angew. Chem. 2011, 123, 12813
49. Angew. Chem. Int. Ed. 2011, 50, 12605
50. U. Rinner, C. Lentsch, C. Aichinger, Synthesis 2010, 3763.
51. C.-H. Wei, S. Mannathan, C.-H. Cheng, J. Am. Chem. Soc. 2011, 133, 6942.
52. CCDC885584 (an (S,S)-tosylated derivative of 3 a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
53. G. Hilt, J. Treutwein, Angew. Chem. 2007, 119, 8653
54. Angew. Chem. Int. Ed. 2007, 46, 8500
55. J. Treutwein, G. Hilt, Angew. Chem. 2008, 120, 6916
56. Angew. Chem. Int. Ed. 2008, 47, 6811
57. S. Mannathan, C.-H. Cheng, Chem. Commun. 2010, 46, 1923
58. B. M. Trost, A. B. Pinkerton, D. J. Kremzow, J. Am. Chem. Soc. 2000, 122, 12007
59. B. M. Trost, A. McClory, Org. Lett. 2006, 8, 3627.