(S,S)-(+)-Pseudoephedrine as chiral auxiliary in asymmetric acetate aldol reactions

Organic and Biomolecular Chemistry

Volumn 3, Issue 10, 2005, Pages 2026-2030

  Rodríguez, Mónica ^a   Vicario, Jose L ^a   Badía, Dolores ^a   Carrillo, Luisa ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ADDITIVES; ALDEHYDES; CHEMICAL BONDS; ISOMERS; STEREOCHEMISTRY;

ACETATE; ALDOL REACTIONS; ENOLATE; PSEUDOEPHEDRINE;

SYNTHESIS (CHEMICAL);

EID: 19944382553     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b502995c     Document Type: Article

References (45)

1. Reviews on the asymnetric aldol reaction: (a) C. Palomo, M. Oiarbide and J. M. Garcia, Chem. Soc. Rev., 2004, 33, 65;
2. (b) C. Palomo, M. Oiarbide and J. M. Garcia, Chem. Eur. J., 2002, 8, 37;
3. (c) B. Alcaide and P. Almendros, Eur. J. Org. Chem., 2002, 1595;
4. (d) T. D. Machajewski and C.-H. Wong, Angew. Chem., Int. Ed., 2000, 39, 1352;
5. (e) R. Mahrwald, Chem. Rev., 1999, 99, 1095;
6. (f) E. M. Carreira, in Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Heidelberg, 1999, vol. 3, p. 997;
7. (g) S. G. Nelson, Tetrahedron: Asymmetry, 1998, 9, 357;
8. (h) H. Groger, E. M. Vogl and M. Shibasaki, Chem. Eur. J., 1998, 4, 1137;
9. (i) M. Braun, in Stereoselective Synthesis, Houben-Weyl, ed. G. Helmchen, R. Hoffmann, J. Mulzer and E. Schaumann, Thieme, Stuttgart, 1996, vol. E21/3, p. 1603;
10. (j) C. J. Cowden and I. Paterson, Org. React., 1997, 51, 1.
11. (a) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley and Sons, New York, 1995. See also:
12. (b) P. Arya and H. Quin, Tetrahedron, 2000, 56, 917.
13. Representative examples of total syntheses involving asymmetric aldol reactions can be found in: (a) K. C. Nicolau and E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996;
14. (b) K. C. Nicolau and S. A. Zinder, Classics in Total Synthesis II, VCH, Weinheim, 2003.
15. J. L. Vicario, D. Badía, E. Domínguez, M. Rodríguez and L. Carrillo, J. Org. Chem., 2000, 65, 3754.
16. For other uses of pseudoephedrine as chiral auxiliary see: (a) A. G. Myers and M. G. Charest, in Handbook of Reagents for Organic Synthesis: Chiral Reagents for Asymmetric Synthesis, ed. L. A. Paquette, Wiley Interscience, New York, 2003, p. 485.
17. See also: (b) J. Echebarria, J. L. Vicario, D. Badia and L. Carrillo, J. Org. Chem., 2004, 69, 2588
18. (c) P. C. Hutchison, T. D. Heightman and D. J. Procter, J. Org. Chem., 2004, 69, 790
19. (d) J. H. Smitrovich, G. N. Boice, C. Qu, L. Dimichelle, T. D. Nelson, M. A. Huffman, J. Murry, J. McNamara and P. J. Reider, Org. Lett., 2002, 4, 1963
20. (e) P. C. Hutchison, T. D. Heightman and D. J. Procter, Org. Lett., 2002, 4, 4583
21. (f) J. L. Vicario, D. Badía and L. Carrillo, J. Org. Chem., 2001, 66, 5801.
22. J. L. Vicario, D. Badía and L. Carrillo, Tetrahedron: Asymmetry, 2003, 14, 489.
23. For an excellent discussion about the problems of the acetate-type aldol reaction see: M. Braun, Angew. Chem., Int. Ed. Engl., 1987, 26, 24. See also refs. 5a and 5d.
24. Some relevant examples: (a) Y. Zang and T. Sammakia, Org. Lett., 2004, 6, 3139;
25. (b) Y. Zhang, A. J. Phillips and T. Sammakia, Org. Lett., 2004, 6, 23;
26. (c) N. R. Guz and A. J. Philips, Org. Lett., 2002, 4, 2253;
27. (d) Y.-C. Wang, D.-W. Su, C.-M. Lin, H.-L. Tseng, C.-L. Li and T.-H. Yan, J. Org. Chem.. 1999, 64, 6495;
28. (e) S. Saito, K. Hatanaka, T. Kanoand H. Yamamoto, Angew. Chem., Int. Ed. Engl., 1998, 37, 3378;
29. (f) C. Palomo, A. González, J. M. García, C. Landa, M. Oiarbide, S. Rodríguez and A. Linden, Angew. Chem., Int. Ed. Engl., 1998, 37, 180;
30. (g) A. González, J. Aiguadé, F. Urpí and J. Vilarrasa, Tetrahedron Lett., 1996, 37, 8949;
31. (h) M. Braun and S. Gräf, Org. Synth., 1995, 72, 38;
32. (i) Z. Pakulski and A. Zamojski, Tetrahedron, 1995, 51, 871;
33. (j) S. G. Davies, H. M. Kellie and R. Polywka, Tetrahedron: Asymmetry, 1994, 5, 2563;
34. (k) W. Oppolzer, J. Blagg, I. Rodríguez and E. Walther, J. Am. Chem. Soc., 1990, 112, 2767;
35. (l) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiani, T. Inoue, K. Hashimoto and E. Fujita, J. Org. Chem., 1986, 51, 2391;
36. (m) M. Braun and R. Devant, Angew. Chem., Int. Ed. Engl., 1983, 12, 788;
37. (n) H. Eichenauer, E. Friedrich, W. Lutz and D. Enders, Angew. Chem., Int. Ed. Engl., 1978, 17, 206.
38. Pseudoephedrine has shown to be an excellent chiral auxiliary in acetate aldol additions with chiral aldehydes, under double stereodifferentiation conditions: J. L. Vicario, M. Rodríguez, D. Badía, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
39. (a) K. Rück, Angew. Chem., Int. Ed. Engl., 1995, 34, 433;
40. (b) K. W. Henderson, A. E. Dorigo, Q.-Y. Liu, P. G. Williard, P. v. R. Schleyer and P. R. Bernstein, J. Am. Chem. Soc., 1996, 118, 1339 and references therein. See also references 5a and 5d.
41. S. E. Denmark, T. Wynn and G. L. Beutner, J. Am. Chem. Soc., 2002, 124, 13405.
42. J. L. Vicario, D. Badia, E. Domínguez and L. Carrillo, J. Org. Chem., 1999, 64, 4610.
43. See for example: (a) L. N. Pridgen, A. F. Abdel-magid, I. Lantos, S. Shilerat and D. S. Eggleston, J. Org. Chem. 1993, 58, 5107 and references therein.
44. See also: (b) J. M. Goodman, S. D. Kahn and I. Paterson, J. Org. Chem., 1990, 55, 3295.
45. Y. Li, M. N. Paddon-Row and K. N. Houk, J. Am. Chem. Soc., 1988, 110, 3684.