A lewis acid-lewis base bifunctional catalyst from a new mixed ligand

Organic Letters

Volumn 9, Issue 4, 2007, Pages 567-570

  Lin, Yun Ming ^a   Boucau, Julie ^a   Li, Zhongtao ^a   Casarotto, Virginie ^a   Lin, Jinzhen ^a   Nguyen, Annie N ^a   Ehrmantraut, Jessica ^a  

^a UNIVERSITY OF TOLEDO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847779186     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0626903     Document Type: Article

References (33)

1. (a) Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: New York, 1999; Vols. 1 and 2.
2. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H. Eds.; Springer: New York, 1999; Vols. I-III.
3. (c) For an example of Lewis acid activation by Lewis base, see: Denmark, S. E.; Beutner, G. L.; Wynn, T.; Eastgate, M. D. J. Am. Chem. Soc. 2005, 127, 3774-3789.
4. (a) Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691-1693.
5. (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325-335.
6. For an overview, see: (a) Katsuki, T. Synlett 2003, 281-297.
7. (b) For practical consideration, see: Cozzi, P. G. Chem. Soc. Rev. 2004, 33, 410-421.
8. (c) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801-2803.
9. (d) Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett. 1990, 31, 7345-7348.
10. (a) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168.
11. (b) Cortez, G. S.; Tennyson, R. L.; Romo, D. J. Am. Chem. Soc. 2001, 123, 7945-7946.
12. For reviews, see: (c) Frances, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985-3012.
13. (d) Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965-2983.
14. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989-1999.
15. (b) Ma, J.-A.; Cahard, D. Angew. Chem., Int. Ed. 2004, 43, 4566-4583. For examples of Lewis acid-Lewis base bifunctional catalysts, see:
16. (c) Sibi, M. P.; Cook, G. R.; Liu, P. Tetrahedron Lett. 1999, 40, 2477-2480.
17. (d) Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594-11599.
18. (e) DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2001, 3, 3053-3056.
19. (f) France, S.; Wack, H.; Hafez, A. M.; Taggi, A. E.; Witsil, D. R.; Lectka, T. Org. Lett. 2002, 4, 1603-1605.
20. (g) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206-1215.
21. (h) Lundgren, S.; Wingstrand, E.; Penhoat, M.; Moberg, C. J. Am. Chem. Soc. 2005, 127, 11592-11593.
22. (a) Nelson, S. G.; Zhu, C.; Shen, X. J. Am. Chem. Soc. 2004, 126, 14-15.
23. (b) Zhu, C.; Shen, X.; Nelson, S. G. J. Am. Chem. Soc. 2004, 126, 5352-5353.
24. (c) Calter, M. A.; Tretyak, O. A.; Flascheriem, C. Org. Lett. 2005, 7, 1809-1812.
25. (d) Gnanadesikan, V.; Corey, E. J. Org. Lett. 2006, 8, 4943-4945.
26. (e) Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2004, 43, 6358-6360.
27. For examples of catalyst discovery through screening, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902.
28. (b) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285.
29. For reviews, see: (a) Wang, Y.; Tennyson, R. L.; Romo, D. Heterocycles 2004, 64, 605-658.
30. (b) Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403-6434.
31. Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125-2128.
32. For a review on chiral metallosalen complexes, see: (a) Katsuki, T. Adv. Synth. Catal. 2002, 344, 131-147.
33. For structrual studies of a Salen-Co(II) complex, see: (b) Leung, W.-H.; Chan, E. Y. Y.; Chow, E. K. F.; Williams, I. D.; Peng, S.-M. J. Chem. Soc., Dalton Trans. 1996, 1229-1236.