Cationic palladium complex catalyzed highly enantioselective intramolecular addition of arylboronic acids to ketones. A convenient synthesis of optically active cycloalkanols

Journal of the American Chemical Society

Volumn 128, Issue 51, 2006, Pages 16504-16505

  Liu, Guixia ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CATION; CYCLOALKANOL DERIVATIVE; KETONE DERIVATIVE; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ACIDITY; ADDITION REACTION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHIRALITY; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; QUANTUM YIELD; REACTION ANALYSIS;

ACETYLATION; ALCOHOLS; BORONIC ACIDS; CATALYSIS; CATIONS; CYCLIZATION; KETONES; MOLECULAR STRUCTURE; OPTICAL ROTATION; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 33845955214     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0672425     Document Type: Article

References (47)

1. For recent reviews, see: (a) Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2004, 43, 284.
2. (b) Soai, K.; Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 2004; Suppl. 1, pp 95-106.
3. (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
4. (b) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
5. (a) Betancort, J. M.; García, C.; Walsh, P. J. Synlett 2004, 749
6. (b) Jeon, S.-J.; Li, H.; García, C.; LaRochelle, L. K.; Walsh, P. J. J. Org. Chem. 2005, 70, 448.
7. (c) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
8. (d) Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2006, 128, 12660.
9. (e) Mikami, K.; Aikawa, K.; Kainuma, S.; Kawakami, Y.; Saito, T.; Sayo, N.; Kumobayashi, H. Tetrahedron: Asymmetry 2004, 15, 3885.
10. (a) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445.
11. (b) Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124, 14850.
12. (c) García, C.; Walsh, P. J. Org. Lett. 2003, 5, 3641.
13. (d) Li, H.; García, C; Walsh, P. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5425.
14. (e) Pieto, O.; Ramon, D. J.; Yus, M. Tetrahedron: Asymmetry 2003, 14, 1955.
15. Rh-catalyzed enantioselective addition of arylboronic acids to aldehydes, see: (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279.
16. (b) Duan, H.-F.; Xie, J.-H.; Shi, W.-J.; Zhang, Q.; Zhou, Q.-L. Org. Lett. 2006, 8, 1479.
17. (c) Suzuki, K.; Ishii, S.; Kondo, K.; Aoyama, T. Synlett 2006, 648.
18. Rh-catalyzed addition of organometallic reagents to simple ketones, see: (a) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733.
19. (b) Oi, S.; Moro, M.; Fukuhara, H.; Kawanishi, T.; Inoue, Y. Tetrahedron 2003, 59, 4351.
20. (c) Ueura, K.; Miyamura, S.; Satoh, T.; Miura, M. J. Organomet. Chem. 2006, 691, 2821.
21. (a) Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353.
22. (b) Toullec, P. Y.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2006, 8, 2715.
23. For a recent review, see: Yamamoto, Y.; Nakamura, I. Top. Organomet. Chem. 2005, 14, 211 and references therein.
24. Pd(0)-catalyzed arylation of ketones and nitriles, see: (a) Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827.
25. (b) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587.
26. (c) Pletnev, A. A.; Larock, R. C. Tetrahedron Lett. 2002, 43, 2133.
27. (d) Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2002, 67, 9428.
28. Pd(II)-catalyzed arylation of aldehydes and nitriles, see: (a) Yamamoto, T.; Ohta, T.; Ito, Y. Org. Lett. 2005, 7, 4153.
29. (b) Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302.
30. (c) Zhou, C.; Larock, R. C. J. Org. Chem. 2006, 71, 3551.
31. (d) Zhao, B.; Lu, X. Tetrahedron Lett. 2006, 47, 6765.
32. (e) Suzuki, K.; Arao, T.; Ishii, S.; Maeda, Y.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2006, 47, 5789.
33. Pd(II)-catalyzed 1,2-addition of aldehydes and ketones initiated by acetoxypalladation of alkynes, see: (a) Zhao, L.; Lu, X. Angew. Chem., Int. Ed. 2002, 41, 4343.
34. (b) Lu, X. Top. Catal. 2005, 35, 73.
35. Mikami, K.; Hatano, M.; Akiyama, K. Top. Organomet. Chem. 2005, 14, 279 and references therein.
36. Stang, P. J.; Cao, D. H.; Poulter, G. T.; Arif, A. M. Organometallics 1995, 14, 1110.
37. The additive base is necessary to prevent the product for further dehydration to benzofuran. Ghosh, S.; Datta, I.; Chakraborty, R.; Das, T. K.; Sengupta, J.; Sarkar, D. C. Tetrahedron 1989, 45, 1441.
38. For recent selected examples catalyzed by 4, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474.
39. (b) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450.
40. (c) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240.
41. (d) Hamashima, Y.; Somei, H.; Shimura, Y.; Tamura, T.; Sodeoka, M. Org. Lett. 2004, 6, 1861.
42. (e) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem., Int. Ed. 2005, 44, 1525.
43. The substrates were easily synthesized by trapping the corresponding arylmetal intermediates with borates (see Supporting Information).
44. (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Organometallics 2004, 23, 4317.
45. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
46. (c) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
47. Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.