Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes

Chemistry - A European Journal

Volumn 21, Issue 27, 2015, Pages 9666-9670

  Yasuda, Yuto ^a   Nagao, Kazunori ^a   Shido, Yoshinori ^a   Mori, Seiji ^b   Ohmiya, Hirohisa ^a   Sawamura, Masaya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b IBARAKI UNIVERSITY   (Japan)

Author keywords

allylic substitution; copper catalysis; coupling; secondary alkylborane; stereoselectivity

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; COPPER; COUPLINGS; PHOSPHATES; STEREOSELECTIVITY; SUBSTITUTION REACTIONS;

ALLYLIC PHOSPHATES; ALLYLIC SUBSTITUTION; COPPER CATALYSIS; COPPER CATALYZED; COPPER-CATALYZED COUPLINGS; ORGANOBORON COMPOUND; SECONDARY ALKYLBORANE; TRIPHENYL PHOSPHINES;

COPPER COMPOUNDS;

EID: 84934996894     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501055     Document Type: Article

References (30)

1. For a review on transition-metal-catalyzed allylic substitutions with organoboron compounds, see:, F. C. Pigge, Synthesis 2010, 1745-1762.
2. A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785
3. C. A. Falciola, A. Alexakis, Eur. J. Org. Chem. 2008, 3765-3780
4. A. Alexakis, J. E. Bäckvall, N. Krause, O. Pàmies, M. Diéguez, Chem. Rev. 2008, 108, 2796-2823
5. S. R. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minnaard, B. L. Feringa, Chem. Rev. 2008, 108, 2824-2852.
6. H. Ohmiya, U. Yokobori, Y. Makida, M. Sawamura, J. Am. Chem. Soc. 2010, 132, 2895-2897
7. K. Nagao, H. Ohmiya, M. Sawamura, Synthesis 2012, 44, 1535-1541
8. K. Nagao, U. Yokobori, Y. Makida, H. Ohmiya, M. Sawamura, J. Am. Chem. Soc. 2012, 134, 8982-8987. See also
9. A. M. Whittaker, R. P. Rucker, G. Lalic, Org. Lett. 2010, 12, 3216-3218.
10. Y. Shido, M. Yoshida, M. Tanabe, H. Ohmiya, M. Sawamura, J. Am. Chem. Soc. 2012, 134, 18573-18576
11. K. Hojoh, Y. Shido, H. Ohmiya, M. Sawamura, Angew. Chem. Int. Ed. 2014, 53, 4954.
12. H. Ohmiya, N. Yokokawa, M. Sawamura, Org. Lett. 2010, 12, 2438-2440
13. R. Shintani, K. Takatsu, M. Takeda, T. Hayashi, Angew. Chem. Int. Ed. 2011, 50, 8656-8659
14. Angew. Chem. 2011, 123, 8815-8818
15. B. Jung, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 1490-1493
16. F. Gao, J. L. Carr, A. H. Hoveyda, Angew. Chem. Int. Ed. 2012, 51, 6613-6617
17. Angew. Chem. 2012, 124, 6717-6721
18. M. Takeda, K. Takatsu, R. Shintani, T. Hayashi, J. Org. Chem. 2014, 79, 2354-2367.
19. For a review on copper-mediated 1,3-syn selective allylic substitutions of organometallic reagents by employing reagent-directing leaving groups, see:, B. Breit, Y. Schmidt, Chem. Rev. 2008, 108, 2928-2951.
20. Reaction of (S)-(E)- 3 a proceeded with significantly decreased E-selectivity (E/Z 59:41), consistent with the concept of allylic 1,3-strain in acyclic stereocontrol. See:, R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860.
21. C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293-1316
22. I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063-2192
23. L. Chabaud, P. James, Y. Landais, Eur. J. Org. Chem. 2004, 3173-3199.
24. M. A. Kacprzynski, T. L. May, S. A. Kazane, A. H. Hoveyda, Angew. Chem. Int. Ed. 2007, 46, 4554-4558
25. Angew. Chem. 2007, 119, 4638-4642
26. F. Gao, K. P. McGrath, Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 14315-14320. For the synthesis of allylsilanes via copper-catalyzed allylic substitutions with silylating reagents, see
27. D. J. Vyas, M. Oestreich, Chem. Commun. 2010, 46, 568-570
28. D. J. Vyas, M. Oestreich, Angew. Chem. Int. Ed. 2010, 49, 8513-8515
29. Angew. Chem. 2010, 122, 8692-8694.
30. For the synthesis of enantioenriched allylsilanes through palladium-catalyzed allylic substitutions of enantioenriched γ-silylated secondary allylic alcohol derivatives with organoboronic acids, see:, D. Li, T. Tanaka, H. Ohmiya, M. Sawamura, Org. Lett. 2010, 12, 3344-3347.