Stereoselective borylative ketone-diene coupling

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5267-5269

  Cho, Hee Yeon ^a   Yu, Zhiyong ^a   Morken, James P ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; KETONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

BORON; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 80054751613     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202138v     Document Type: Article

References (46)

1. See http://cbc.arizona.edu/njardarson/group/top-pharmaceuticals- poster.
2. Reviews: Hatano, M; Ishihara, K. Synthesis 2008, 1647.
3. Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853.
4. Garcia, C.; Martin, V. S. Curr. Org. Chem. 2006, 10, 1849.
5. Cho, H. Y.; Morken, J. P. J. Am. Chem. Soc. 2008, 130, 16140.
6. Cho, H. Y.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 7576.
7. For related reductive or alkylative Ni-catalyzed diene carbonyl couplings, see: Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033.
8. Takimoto, M.; Hiraga, Y.; Sato, Y.; Mori, M. Tetrahedron Lett. 1998, 39, 4543.
9. Sato, Y.; Takanashi, T.; Hoshiba, M.; Mori, M. Tetrahedron Lett. 1998, 39, 5579.
10. Sato, Y.; Saito, N.; Mori, M. Tetrahedron 1998, 54, 1153.
11. Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371.
12. Kimura, M.; Shibata, K.; Koudahashi, Y.; Tamaru, Y. Tetrahedron Lett. 2000, 41, 6789.
13. Shibata, K.; Kimura, M.; Kojima, K.; Tanaka, S.; Tamaru, Y. J. Organomet. Chem. 2001, 624, 348.
14. Sato, Y.; Sawaki, R.; Mori, M. Organometallics 2001, 20, 5510.
15. Shibata, K.; Kimura, M.; Shimizu, M.; Tamaru, Y. Org. Lett. 2001, 3, 2181.
16. Sato, Y.; Saito, N.; Mori, M. J. Org. Chem. 2002, 67, 9310.
17. Sato, Y.; Sawaki, R.; Saito, N.; Mori, M. J. Org. Chem. 2002, 67, 656.
18. Loh, T.-P.; Song, H.-Y.; Zhou, Y. Org. Lett. 2002, 4, 2715.
19. Takimoto, M.; Kajima, Y.; Sato, Y.; Mori, M. J. Org. Chem. 2005, 70, 8605.
20. Hirashita, T.; Kambe, S.; Tsuji, H.; Araki, S. Chem. Commun. 2006, 2595.
21. For reviews and selected recent examples of related nickelcatalyzed couplings, see: Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
22. Kimura, M.; Tamaru, Y. Top. Curr. Chem. 2007, 279, 173.
23. Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 4441.
24. Ho, C.-Y.; Jamison, T. F. Angew. Chem., Int. Ed. 2007, 46, 782.
25. Baxter, R. D.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 9662.
26. Ng, S.-S.; Ho, C.-Y.; Schleicher, K. D.; Jamison, T. F. Pure Appl. Chem. 2008, 80, 929.
27. Liu, P.; McCarren, P.; Cheong, P. H.-Y.; Jamison, T. F.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 2050.
28. Malik, H. A.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc. 2010, 132, 6304.
29. For aligned studies in dienećarbonyl couplings, see: Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340.
30. Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891.
31. Kim, I. S.; Han, S. B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514.
32. Skucas, E.; Zbieg, J. R.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 5054.
33. Han, S. B.; Han, H.; Krische,M. J. J. Am. Chem. Soc. 2010, 132, 1760.
34. Han, S. B.; Gao, X.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 9153.
35. For dienećarbonyl couplings that employ ketones, see: Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
36. Sato, Y.; Takimoto, M.; Mori, M. Tetrahedron Lett. 1996, 37, 887.
37. Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397.
38. Kimura, M.; Matsuo, S.; Shibata, K.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 3386.
39. Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624.
40. Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784.
41. Kimura, M.; Kojima, K.; Tamaru, Y. Synthesis 2004, 3089.
42. Kimura, M.; Ezoe, A.; Mori, M.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 201.
43. Kimura, M.; Ezoe, A.; Mori, M.; Iwata, K.; Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 8559.
44. Saito, N.; Yamazaki, T.; Sato, Y. Chem. Lett. 2009, 38, 594.
45. Saito, N.; Yamazaki, T.; Sato, Y. Tetrahedron Lett. 2008, 49, 5073.
46. Ogoshi, S.; Tonomori, K.; Oka, M.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 7077.