Direct catalytic asymmetric aldol-Tishchenko reaction

Journal of the American Chemical Society

Volumn 126, Issue 25, 2004, Pages 7782-7783

  Gnanadesikan, Vijay ^a   Horiuchi, Yoshihiro ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PROPIONIC ACID;

ALDOL TISHCHENKO REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 3042687996     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047906f     Document Type: Article

References (29)

1. For a recent review, see: Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
2. (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
3. (b) Yoshikawa, N,; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168.
4. (c) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2466.
5. (a) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12033.
6. (b) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395.
7. (c) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
8. (d) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
9. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
10. (f) Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852.
11. For the first example of direct aldol reaction of ethyl ketones, see: (a) Mahrwald, R. Org. Lett. 2000, 2, 4011.
12. (b) Mahrwald, R.; Ziemer, B. Tetrahedron Lett. 2002, 43, 4459.
13. Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706 and references therein.
14. (a) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
15. (b) Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem. Int. Ed. 2001, 40, 601.
16. For racemic reactions, see: (a) Mascarenhas, C. M.; Duffy, M. O.; Liu, S. Y.; Morken, J. P. Org. Lett. 1999, 1, 1427.
17. (b) Bodnar, P. M.; Shaw, J. T.; Woerpel, K. A. J. Org. Chem. 1997, 62, 5674.
18. (c) Simpura, I.; Nevalainen, V. Tetrahedron Lett. 2001, 42, 3905.
19. (d) Mahrwald, R.; Costisella, B. Synthesis 1996, 1087.
20. (e) Loog, O.; Maeorg, U. Tetrahedron: Asymmetry 1999, 10, 2411.
21. (t) Schneider, C.; Hansch, M. Chem. Commun. 2001, 1218 and references therein.
22. For a moderately enantioselective reaction, see: (a) Schneider, C.; Hansch, M. Synlett 2003, 837.
23. Diastereomeric ratio represents major anti-aldol anti-Tishchenko isomer versus all minor diastereomers.
24. Other metal salts such as NaOTf, KOTf, CuOTf, and Mg(OTf)2 produced less satisfactory results.
25. Relative and absolute configurations were determined by chemical correlation and X-ray analysis. See Supporting Information for more details.
26. For mechanistic studies dealing with the reversibility of aldol reaction, see refs 6b and 7a as well as: (a) Lu, L.; Chang, H. Y.; Fang, J. M. J. Org. Chem. 1999, 64, 843.
27. (b) Abu-Hasanayn, F.; Streitwieser, A. J. Org. Chem. 1998, 63, 2954.
28. Slightly lower ee would be ascribed to the different starting materials used. See Supporting Information for details.
29. Presumably, the low aldol selectivities are due to strong retro-aldolization.