Deconstructing quinine. Part 1. Toward an understanding of the remarkable performance of cinchona alkaloids in asymmetric phase transfer catalysis

Heterocycles

Volumn 82, Issue 2, 2010, Pages 1527-1540

  Denmark, Scott E ^a   Weintraub, Robert C ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952743032     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-S(E)108     Document Type: Article

References (40)

1. T. S. Kaufman and E. A. Rúveda, Angew. Chem. Int. Ed., 2005, 44, 854.
2. C. E. Song, 'Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, Wiley-VCH, Weinheim, 2009;
3. K. Kacprzak and J. Gawronski, Synthesis, 2001, 961.
4. S.-S. Jew and H.-G. Park, Chem. Commun., 2009, 7090.
5. S. G. Hentges and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 4263.
6. T. Marcelli and H. Hiemstra, Synthesis, 2010, 1229.
7. T. P. Yoon and E. N. Jacobsen, Science, 2003, 299, 1691.
8. C. M. Starks, J. Am. Chem. Soc, 1971, 93, 195.
9. U.-H. Dolling, P. Davis, and E. J. J. Grabowski, J. Am. Chem. Soc, 1984, 106, 446.
10. M. J. O'Donnell, W. D. Bennett, and S. Wu, J. Am. Chem. Soc, 1989, 111, 2353.
11. M. J. O'Donnell, S. Wu, and J. C. Huffman, Tetrahedron, 1994, 50, 4507.
12. B. Lygo and P. G. Wainwright, Tetrahedron Lett, 1997, 38, 8595.
13. E. J. Corey, F. Xu, and M. C. Noe, J. Am. Chem. Soc, 1997, 119, 12414;
14. E. J. Corey, Y. Bo, and J. Busch-Peterson, J. Am. Chem. Soc., 1998, 120, 13000.
15. Z. G. Hajos and D. R. Parrish, J. Org. Chem, 1974, 39, 1615;
16. U. Eder, G. Sauer, and R. Wiechert, Angew. Chem. Int., Ed. Engl., 1971, 83, 492;
17. B. List, R. A. Lerner, and C. F. Barbas III, J. Am. Chem. Soc., 2000, 122, 2395.
18. B.-L. Zheng, Q.-Z. Liu, C.-S. Guo, X.-L. Wang, and L. He, Org. Biomol. Chem, 2007, 5, 2913.
19. B. Wang, F. Wu, Y. Wang, X. Liu, and L. Deng, J. Am. Chem. Soc, 2007, 129, 768.
20. L.-W. Xu, J. Luo, and Y. Lu, Chem. Commun, 2009, 1807.
21. B. Lygo, J. Crosby, T. R. Lowdon, and P. G. Wainwright, Tetrahedron, 2001, 57, 2391.
22. E. V. Dehmlow, S. Düttmann, B. Neumann, and H.-G. Stammler, Eur. J. Org. Chem, 2002, 2087.
23. S.-S. Jew, M.-S. Yoo, B.-S. Jeong, Y. Park, and H.-G. Park, Org. Lett, 2002, 4, 4245.
24. M.-S. Yoo, B.-S. Jeong, J.-H. Lee, H.-G. Park, and S.-S. Jew, Org. Lett, 2005, 7, 1129.
25. K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, and M. J. O'Donnell, J. Org. Chem, 1991, 56, 5181.
26. D. L. Hughes, U.-H. Dolling, K. M. Ryan E. F. Schoenewaldt, and E. J. J. Grabowski, J. Org. Chem, 1987, 52, 4745.
27. S.-S. Jew and H.-G. Park, 'Asymmetric Phase Transfer Catalysis', ed. by K. Maruoka, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008, pp. 49-70.
28. A. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris, and T. Lectka, J. Am. Chem. Soc, 2002, 124, 6625.
29. C. Bucher, C. Sparr, W. B. Schweizer, and R. Gilmour, Chem. Eur. J, 2009, 19, 7637.
30. D. H. R. Barton and S. W. McCombie, J. Chem. Soc., Perkin Trans. 1, 1975, 1574;
31. D. H. R. Barton and J. Cs. Jaszberenyi, Tetrahedron Lett, 1989, 30, 2619.
32. L. Somekh and A. Shanzer, J. Am. Chem. Soc, 1982, 104, 5836.
33. J.-H. Lee, M.-S. Yoo, J.-H. Jung, S.-S. Jew, H.-G. Park, and B.-S. Jeong, Tetrahedron, 2007, 63, 7906.
34. 2)
35. Whereas the Jew-Park model for enantioselectivity invokes the E-configuration of the enolate, Lipkowitz, O'Donnell and coworkers found that binding of the less stable Z-enolate leads to a better computational correlation with the observed alkylation selectivities. K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, and M. J. O'Donnell, J. Org. Chem, 1991, 56, 5181.
36. For a discussion of the reasons that organofluorine compounds do not form strong hydrogen bonds see: J. D. Dunitz, ChemBioChem, 2004, 5, 614.
37. (a) C. M. Starks, C. L. Liotta, and M. Halpern, 'Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives', Chapman and Hall: New York, 1994, pp. 89-108;
38. (b) A. Brandstrom, Adv. Phys. Org. Chem., 1978, 15, 267;
39. (c) M. Rabinovitz, Y. Cohen, and M. Halpern, Angew. Chem., Int. Ed. Engl., 1986, 25, 960.
40. S. E. Denmark, N. D. Gould, and L. M. Wolf, J. Am. Chem. Soc., manuscript submitted.