Chiral lithium amides on polymer support - Synthesis and use in deprotonation of ketones

Canadian Journal of Chemistry

Volumn 84, Issue 2, 2006, Pages 257-268

  Majewski, Marek ^a   Ulaczyk Lesanko, Agnieszka ^a   Wang, Fan ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Chiral lithium amides; Deprotonation; Enolates; Polymer supported reagents; Tropinone

Indexed keywords

ALCOHOLS; KETONES; POLYSTYRENES; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

CHIRAL LITHIUM AMIDES; DEPROTONATION; ENOLATES; POLYMER-SUPPORTED REAGENTS; TROPINONE;

LITHIUM COMPOUNDS;

CARBONYL DERIVATIVE; KETONE; LITHIUM; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; POLYMERIZATION; RING OPENING; SYNTHESIS;

EID: 33744935042     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-006     Document Type: Article

References (50)

1. D.J. Gravert and K.D. Janda. Chem. Rev. 97, 489 (1997).
2. (a) C.R. Harrison, P. Hodge, B.J. Hunt, E. Khoshedel, and G. Richardson. J. Org. Chem. 48, 3721 (1983);
3. (b) J.S. Fruchtel and G. Jung. Angew. Chem. Int. Ed. Engl. 35, 17 (1996);
4. (c) A.R. Vaino and K.D. Janda. J. Comb. Chem. 2, 579 (2000);
5. (d) C.W. Harwing, J. Graven, and K.D. Janda. Chemtracts, 12, 1 (1999);
6. (e) P.H. Toy and K.D. Janda. Acc. Chem. Res. 33, 546 (2000).
7. J.A. Gladysz. Chem. Rev. 102, 3215 (2002), and other papers in this special issue
8. (a) M. Majewski. In Advances in asymmetric synthesis. Vol. 3. Edited by A. Hassner. JAI Press, London. 1998, p. 39;
9. (b) M. Majewski and F. Wang. Tetrahedron, 58, 4567 (2002);
10. (c) M. Majewski, M. DeCaire, P. Nowak, and F. Wang. Can. J. Chem. 79, 1792 (2001);
11. (d) M. Majewski and P. Nowak. J. Org. Chem. 65, 5152 (2000);
12. (e) M. Majewski, R. Lazny, and A. Ulaczyk. Can. J. Chem. 75, 754 (1997);
13. (f) M. Majewski and R. Lazny. Synlett, 785 (1996);
14. (g) Review of enantioselective deprotonation with chiral lithium amide bases: P.J. O'Brien. J. Chem. Soc. Perkin Trans, 1, 1439 (1998).
15. B.J. Cohen, M.A. Kraus, and A. Patchornik. J. Am. Chem. Soc. 103, 7620 (1981).
16. M. Majewski, A. Ulaczyk, and F. Wang. Tetrahedron Lett. 40, 8755 (1999).
17. (a) A. Seki, Y. Takizawa, F. Ishiwata, and M. Asami. Chem. Lett. 32, 342 (2003);
18. (b) A. Johansson, P. Abrahamsson, and O. Davidsson. Tetrahedron: Asymmetry, 14, 1261 (2003);
19. (c) M. Asami and A. Seki. Chem. Lett. 160 (2002);
20. (d) A. Seki and M. Asami. Tetrahedron, 58, 4655 (2002).
21. M.B. Smith and J. March. March's advanced organic chemistry. Wiley, Toronto. 2001. p. 517
22. (a) D. Harris. Quantitative chemical analysis. Freeman, New York. 1987;
23. (b) M. Narita. Bull. Chem. Soc. Jpn. 51, 1477 (1978).
24. C.R. McArthur, P.M. Worster, J. Jiang, and C.C. Leznoff. Can. J. Chem. 60, 1836 (1982).
25. K.S. Lam, M. Lebl, and V. Krchnak. Chem. Rev. 97, 411 (1997).
26. M. Watanabe and K. Soai. J. Chem. Soc. Perkin Trans, 1, 837 (1994).
27. G.L. Lange and C. Gottardo. Synth. Commun. 10, 1473 (1990).
28. G. Liu and J.A. Ellman. J. Org. Chem. 60, 7712 (1995).
29. A. Vidal-Ferran, N. Bampos, A. Moyano, M.A. Pericas, A. Riera, and J.K.M Sanders. J. Org. Chem. 63, 6309 (1998).
30. K.D. Shimizu, M.L. Snapper, and A.H. Hoveyda. Eur. J. Chem. 4, 1885 (1998).
31. P. Wentworth, Jr. and K.D. Janda. Chem. Commun. 1917 (1999).
32. K. Shirai, K. Aoki, D. Sato, H.-D. Kim, M. Murakata, T. Yasuka, and K. Koga. Chem. Pharm. Bull. 42, 690 (1994).
33. (a) T. Honda, S. Ono, H. Mizutani, and K.O. Hallinan. Tetrahedron: Asymmetry, 8, 181 (1997);
34. (b) O. Muraoka, B.Z. Zheng, K. Okumura, E. Tabata, G. Tanabe, and M. Kubo. J. Chem. Soc. Perkin Trans. 1, 113 (1997);
35. (c) M. Nowakowski and H.M.R. Hoffmann. Tetrahedron Lett. 38, 1001 (1997);
36. (d) M. Asami, T. Ishizaki, S. Inoue. Tetrahedron Lett. 36, 1893 (1995);
37. (e) K. Mori and N. Murata. Liebigs Ann. Chem. 2089 (1995);
38. (f) M. Tsukazaki, M. Tinkl, A. Roglans, B.J. Chapell, N.J. Taylor, and V. Snieckus. J. Am. Chem. Soc. 118, 685 (1996);
39. (g) A.J. Blake, S.M. Westaway, and N.S. Simpkins. Synlett, 919 (1997).
40. P. Hodge. Chem. Soc. Rev. 26, 417 (1997).
41. D. Seebach. Angew. Chem. Int. Ed. Engl. 27, 1624 (1988).
42. M. Majewski, R. Lazny, and P. Nowak. Tetrahedron Lett. 36, 5465 (1995).
43. X. Sun and D.B. Collum. J. Am. Chem. Soc. 122, 2452 (2000).
44. T. Laube, J.D. Dunitz, and D. Seebach. Helv. Chim. Acta, 68, 1373 (1985).
45. (a) E. Vedejs and N. Lee. J. Am. Chem. Soc. 113, 5483 (1991);
46. (b) E. Vedejs and N. Lee. J. Am. Chem. Soc. 117, 891 (1995).
47. K. Martinkus, C.-H. Tann, and S.J. Gould. Tetrahedron, 39, 3493 (1983).
48. R.F. Borch, M.D. Bernstein, and H.D. Durst. J. Am. Chem. Soc. 93, 2897 (1971).
49. (a) M. Majewski and G.-Z. Zheng. Can. J. Chem. 70, 2618 (1992);
50. (b) M. Majewski and R. Lazny. J. Org. Chem. 60, 5825 (1995).