Generation of quaternary centers by reductive cross-coupling: Shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2144-2147

  Yang, Dexi ^a   Belardi, Justin K ^b   Micalizio, Glenn C ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

Allylic alcohol; Quaternary center; Reductive cross coupling; Stereoselective synthesis; Titanium alkoxide

Indexed keywords

ALCOHOL; ALLYL COMPOUND; IMINE; TITANIUM;

ARTICLE; CROSS COUPLING REACTION;

EID: 79953230438     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.059     Document Type: Article

References (26)

1. For recent reviews, see: (a) Reichard, H. A.; McLaughlin, M.; Chen, M. Z.; Micalizio, G. C. Eur. J. Org. Chem. 2010, 391;
2. (b) Olan, A.; Six, Y. Tetrahedron 2010, 66, 15;
3. (c) Wolan, A.; Six, Y. Tetrahedron 2010, 66, 3097;
4. (d) Montgomery, J.; Sormunen, G. J. Top. Curr. Chem. 2007, 279, 1;
5. (e) Patman, R. L.; Bower, J. F.; Kim, I. S.; Krische, M. J. Aldrichim. Acta 2008, 41, 95;
6. (f) Jeganmohan, M.; Cheng, C.-H. Chem. Eur. J. 2008, 14, 10876;
7. (g) Moslin, R. M.; Miller-Moslin, K. M.; Jamison, T. F. Chem. Commun. 2007, 4441;
8. (h) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835;
9. (i) Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789.
10. For allylic alcohol-alkyne coupling, see: (a) Kolundzic, F.; Micalizio, G. C. J. Am. Chem. Soc. 2007, 129, 15112;
11. For allylic alcohol-vinylsilane coupling, see: (b) Belardi, J. K.; Micalizio, G. C. J. Am. Chem. Soc. 2008, 130, 16870;
12. For allylic alcohol-imine coupling, see: (c) Takahashi, M.; McLaughlin, M.; Micalizio, G. C. Angew. Chem., Int. Ed. 2009, 48, 3648;
13. (d) Tarselli, M. A.; Micalizio, G. C. Org. Lett. 2009, 11, 4596;
14. (e) Umemura, S.; McLaughlin, M.; Micalizio, G. C. Org. Lett. 2009, 11, 5402;
15. (f) Yang, D.; Micalizio, G. C. J. Am. Chem. Soc. 2009, 131, 17548;
16. For related coupling reactions, see: (g) Lysenko, I. L.; Kim, K.; Lee, H. G.; Cha, J. K. J. Am. Chem. Soc. 2008, 130, 15997;
17. (h) Lysenko, I. L.; Lee, H. G.; Cha, J. K. Org. Lett. 2009, 11, 3132.
18. Chen, M. Z.; McLaughlin, M.; Takahashi, M.; Tarselli, M. A.; Yang, D.; Umemura, S.; Micalizio, G. C. J. Org. Chem., accepted for publication, doi:10.1021/jo101535d.
19. For recent reviews, see: (a) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105;
20. (b) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 36, 5969.
21. (a) Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485;
22. (b) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519;
23. (c) Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K.; Fujii, T.; Furukawa, I. Chem. Lett. 1995, 315;
24. (d) Barluenga, J.; Rodríguez, F.; Álvarez-Rodrigo, L.; Zapico, J. M.; Fañanás, F. J. Chem. Eur. J. 2004, 10, 109.
25. Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614.
26. For examples, where a related mode of reactivity in intramolecular settings was effective for the generation of quaternary centers, see: Degrado, S. J.; Adams, J. A.; Hoveyda, A. H. Inorg. Chim. Acta 2003, 345, 261.