Cu(II)-catalyzed enantioselective aldol condensation between malonic acid hemithioesters and aldehydes

Tetrahedron Letters

Volumn 45, Issue 8, 2004, Pages 1747-1749

  Orlandi, Simonetta ^a   Benaglia, Maurizio ^a   Cozzi, Franco ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Aldol process; Enantiopure benzimidazoles; Enantioselective catalysis; Malonic acid hemithioesters

Indexed keywords

ALDEHYDE; BENZIMIDAZOLE DERIVATIVE; MALONIC ACID DERIVATIVE; TARTARIC ACID;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; DECARBOXYLATION; ENANTIOSELECTIVITY;

EID: 0842326656     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.089     Document Type: Article

References (11)

1. Review: Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. 3, Chapter 29.1:1999;997-1066 Springer, Berlin.
2. Lalic G., Aloise A.D., Shair M.D. J. Am. Chem. Soc. 125:2003;2852-2853.
3. For other decarboxylative aldol reactions see: Tanaka M., Oota O., Hiramatsu H., Fujiwara K. Bull. Chem. Soc. Jpn. 61:1988;2473-2479.
4. Nokami J., Mandai T., Watanabe H., Ohyama H., Tsuji J. J. Am. Chem. Soc. 111:1989;4126-4127.
5. Kourouli T., Kefalas P., Ragoussis N., Ragoussis V. J. Org. Chem. 67:2002;4615-4618.
6. Rosenfeld D.A., Pratt J.W., Richtmyer N.K., Hudson C.S. J. Am. Chem. Soc. 73:1951;5907-5908.
7. Ralph J.T. Synth. Commun. 19:1989;1381-1387.
8. Katrizky A.R., Aslan D.C., Leeming P., Steel P.J. Tetrahedron: Asymmetry. 8:1997;1491-1500.
9. Nuñez M.T., Martín V.S. J. Org. Chem. 55:1990;1828-1932.
10. For an application of chiral benzimidazolium salts see: Orlandi S., Caporale M., Benaglia M., Annunziata R. Tetrahedron: Asymmetry. 14:2003;3827-3830.
11. 3 and with brine. Evaporation of the solvent gave the crude product that was purified by flash chromatography with an 80:20 hexanes-ethyl acetate mixture as eluant to give 3 (30.5 mg) in 53% yield.