Highly enantioselective vinyl additions of vinylaluminum to ketones catalyzed by a titanium(IV) catalyst of (S)-BINOL

Organic Letters

Volumn 11, Issue 3, 2009, Pages 499-502

  Biradar, Deepak Baburao ^a   Gau, Han Mou ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ALUMINUM; BINOL, NAPHTHOL; KETONE; NAPHTHOL DERIVATIVE; ORGANOMETALLIC COMPOUND; TITANIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; ALUMINUM; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; TITANIUM; VINYL COMPOUNDS;

EID: 60849091637     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801999u     Document Type: Article

References (61)

1. (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
2. (b) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
3. (c) Ramón, D. J.; Yus, M. Chem. Rev. 2006, 106, 2126.
4. (a) Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239.
5. (b) Yus, M.; Ramón, D. J.; Prieto, O. Eur. J. Org. Chem. 2003, 2745.
6. (c) Jeon, S.-J.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 9544.
7. (d) Jeon, S.-J.; Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 16416.
8. (e) García, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970.
9. (a) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002,124, 12668.
10. (b) Funabashi, K.; Jachmann, M.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2003, 42, 5489.
11. (a) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538.
12. (b) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 8355.
13. (a) Pu, L. Tetrahedron 2003, 59, 9873, and references cited therein.
14. (b) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895.
15. (c) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448.
16. (d) Chen, C.; Hong, L.; Xu, Z.-Q.; Liu, L.; Wang, R. Org. Lett. 2006, 8, 2277.
17. (a) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445.
18. (b) Prieto, O.; Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 2003,14, 1955.
19. (c) García, C.; Walsh, P. J. Org. Lett. 2003, 5, 3641.
20. (d) Li, H.; García, C.; Walsh, P. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5425.
21. (e) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2004, 43, 284.
22. (f) Forrat, V. J.; Prieto, O.; Ramón, D. J.; Yus, M. Chem.-Eur. J. 2006, 12, 4431.
23. (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003,103, 2763, and references cited therein,
24. (b) Kim, J. G.; Waltz, K. M.; Garcia, I. F.; Kwiatkowski, D.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 12580.
25. (c) Cunningham, A.; Mokal-Parekh, V.; Wilson, C.; Woodward, S. Org. Biomol. Chem. 2004, 2, 741.
26. (d) Lu, J.; Hong, M.-L.; Ji, S.-J.; Teo, Y.-C.; Loh, T.-P. Chem. Commun. 2005, 4217.
27. Wadamoto, M.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 14556.
28. (a) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
29. (b) Canales, E.; Prasad, K. G.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 11572.
30. (a) Ooi, T.; Takahashi, M.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 37, 835.
31. (b) Ishikawa, T.; Ogawa, A.; Hirao, T. J. Am. Chem. Soc. 1998, 120, 5124.
32. (c) Spino, C.; Beaulieu, C. Angew. Chem., Int. Ed. 2000, 39, 1930.
33. (d) Rainier, J. D.; Cox, J. M. Org. Lett. 2000, 2, 2707.
34. (e) Haraguchi, K.; Kubota, Y.; Tanaka, H. J. Org. Chem. 2004, 69, 1831.
35. (f) Wang, B.; Bonin, M.; Micouin, L. Org. Lett. 2004, 6, 3481.
36. (g) Uchiyama, M.; Naka, H.; Matsumoto, Y.; Ohwada, T. J. Am. Chem. Soc. 2004, 126, 10526.
37. (h) Kojima, K.; Kimura, M.; Tamaru, Y. Chem. Commun. 2005, 4717.
38. (a) Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997. 119, 4080.
39. (b) Pagenkopf, B. L.; Carreira, E. M. Tetrahedron Lett. 1998. 39, 9593.
40. (c) Biswas, K.; Prieto, O.; Goldsmith, P. J.; Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 2232.
41. (d) d'Augustin, M.; Palais, L.; Alexakis, A. Angew. Chem., Int. Ed. 2005, 44, 1376.
42. You, J.-S.; Hsieh, S.-H.; Gau, H.-M. Chem. Commun. 2001, 1546.
43. Lee, Y.; Akiyama, K.; Gillingham, D. G.; Brown, M. K.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 446.
44. Kwak, Y.-S.; Corey, E. J. Org. Lett. 2004, 6, 3385.
45. (a) Wu, K.-H.; Gau, H.-M. J. Am. Chem. Soc. 2006, 128, 14808.
46. (b) Hsieh, S.-H.; Chen, C.-A.; Chuang, D.-W.; Yang, M.-C.; Yang, H.-T.; Gau, H.-M. Chirality 2008, 20, 924.
47. (a) Chen, C.-A.; Wu, K.-H.; Gau, H.-M. Angew. Chem., Int. Ed. 2007. 46, 5373.
48. (b) Chen, C.-A.; Wu, K.-H.; Gau, H.-M. Adv. Synth. Catal. 2008. 350, 1626.
49. Ku, S.-L.; Hui, X.-P.; Chen, C.-A.; Gau, H.-M. Chem. Commun. 2007, 3847.
50. Wu, K.-H.; Chuang, D.-W.; Chen, C.-A.; Gau, H.-M. Chem. Commun. 2008, 2343.
51. Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170.
52. (a) Wipf, P.; Nunes, R. L. Tetrahedron 2004, 60, 1269.
53. (b) Wipf, P.; Kendall, C. Chem.-Eur. J. 2002, 8, 1778.
54. (c) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639.
55. (a) Dahmen, S. D.; Bräse, S. Org. Lett. 2001, 3, 4119.
56. (b) Ji, J.-X.; Qiu, L.-Q.; Yip, C. W.; Chan, A. S. C. J. Org. Chem. 2003, 68, 1589.
57. (c) Bräse, S.; Dahmen, S.; Höfener, S.; Lauterwasser, F.; Kreis, M.; Ziegert, R. E. Synlett 2004, 2647.
58. (a) Wilke, G.; Müller, H. Chem. Ber. 1956, 89, 444.
59. (b) Wilke, G.; Müller, H. Justus Liebigs Ann. Chem. 1958, 618, 267.
60. (a) You, J.-S.; Shao, M.-Y.; Gau, H.-M. Organometallics 2000, 19, 3368.
61. (b) Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580.