Lithium acetate-catalyzed crossed aldol reaction between aldehydes and trimethylsilyl enolates generated from other aldehydes

Chemistry Letters

Volumn 34, Issue 4, 2005, Pages 614-615

  Kawano, Yoshikazu ^a,b   Fujisawa, Hidehiko ^a,b   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; LEWIS BASE; LITHIUM ACETATE; LITHIUM DERIVATIVE; SODIUM BOROHYDRIDE; TRIMETHYLSILYL DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 21644487199     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.614     Document Type: Article

References (23)

1. Using Lewis acid: a) T. Mukaiyama, K. Banno, and K. Narasaka, J. Am. Chem. Soc., 96, 7503 (1974).
2. b) T. Mukaiyama and T. Inoue, Chem. Lett., 1976, 559.
3. Via metal enolate: c) C. H. Heathcock, C. T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn, and J. Lampe, J. Org. Chem., 45, 1066 (1980).
4. d) E. Nakamura, S. Yamago, D. Machii, and I. Kuwajima, Tetrahedron Lett., 29, 2207 (1988).
5. Via enamine: e) G. Wittig and A. Hesse, Org. Synth., Coll. Vol. VI, 526 (1988).
6. f) C. F. Barbas, III, Y.-F. Wang, and C.-H. Wong, J. Am. Chem. Soc., 112, 2013 (1990).
7. g) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 116, 8422 (1994).
8. Via titanium enolate: a) R. Mahrwald, B. Costisella, and B. Gündogan, Tetrahedron Lett., 38, 4543 (1997).
9. b) R. Mahrwald, B. Costisella, and B. Gündogan, Synthesis, 1998, 262.
10. c) R. Mahrwald and B. Gündogan, Chem. Commun., 1998, 2273.
11. d) K. Yachi, H. Shinokubo, and K. Oshima, J. Am. Chem. Soc., 121, 9465 (1999).
12. e) Z. Han, H. Yorimitsu, H. Shinokubo, and K. Oshima, Tetrahedron Lett., 41, 4415 (2000).
13. Catalytic enantioselective crossed aldol reaction: S. E. Denmark and S. K. Ghosh, Angew. Chem., Int. Ed., 40, 4759 (2001).
14. Direct enantioselective crossed aldol reaction: A. B. Northrup and D. W. C. MacMillan, J. Am. Chem. Soc., 124, 6798 (2002).
15. Aldol reaction: a) H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 182.
16. b) H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 858.
17. c) T. Mukaiyama, H. Fujisawa, and T. Nakagawa, Helv. Chim. Acta, 85, 4518 (2002).
18. d) T. Nakagawa, H. Fujisawa, and T. Mukaiyama, Chem. Lett., 32, 462 (2003).
19. e) T. Nakagawa, H. Fujisawa, and T. Mukaiyama, Chem. Lett., 32, 696 (2003).
20. f) T. Nakagawa, H. Fujisawa, and T. Mukaiyama, Chem. Lett., 33, 92 (2004).
21. g) T. Nakagawa, H. Fujisawa, Y. Nagata, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 77, 1555 (2004).
22. h) H. Fujisawa, T. Nakagawa, and T. Mukaiyama, Adv. Synth. Catal., 346, 1241 (2004).
23. 4. After filtration and evaporation of the solvent, the crude product was purified by preparative TLC to afford the corresponding 1,3-diol (74.0 mg, 90%) as an colorless oil.