Direct aldol reaction of pyruvic derivatives: Catalytic attempt to synthesize ulosonic acids

European Journal of Organic Chemistry

Volumn , Issue 14, 2012, Pages 2724-2727

  El Sepelgy, Osama ^a   Schwarzer, Darius ^a   Oskwarek, Piotr ^a   Mlynarski, Jacek ^a,b  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Aldol reactions; Asymmetric catalysis; Carbohydrates; Enzymes

Indexed keywords

EID: 84860637583     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201200325     Document Type: Article

References (23)

1. M. Brovetto, D. Gamenara, P. Saenz Méndez, G. A. Seoane, Chem. Rev. 2011, 111, 4346-4403.
2. B. M. Trost, C. S. Brindle, Chem. Soc. Rev. 2010, 39, 1600-1632.
3. D. Enders, A. A. Narine, J. Org. Chem. 2008, 73, 7857-7870.
4. M. Markert, R. Mahrwald, Chem. Eur. J. 2008, 14, 48-48.
5. N. Mase, C. F. Barbas III, Org. Biomol. Chem. 2010, 8, 4043-4050.
6. J. Mlynarski, B. Gut, Chem. Soc. Rev. 2012, 41, 587-596.
7. B. Lindberg, Adv. Carbohydr. Chem. Biochem. 1990, 48, 279-318.
8. F. M. Unger, Adv. Carbohydr. Chem. Biochem. 1981, 38, 323-388.
9. R. Schauer, Adv. Carbohydr. Chem. Biochem. 1982, 40, 131-234.
10. T. Angata, A. Varki, Chem. Rev. 2002, 102, 439-470.
11. A. Banaszek, J. Mlynarski, Stud. Nat. Prod. Chem. 2005, 30, 419-482.
12. I. Hemeon, A. J. Benet, Synthesis 2007, 1899-1926.
13. 4 oxalacetic acid, followed by decarboxylation, see: R. Winzar, J. Philips, M. J. Kiefel, Synlett 2010, 583-586 and references cited therein
14. for the stereoselective aldol condensation of aldoses with lithiated 2-acetylthiasole, see:, A. Dondoni, P. Merino, J. Org. Chem. 1991, 56, 5294-5301.
15. For the reaction with chloral monohydrate, see:, H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. 2004, 116, 2017; Angew. Chem. Int. Ed. 2004, 43, 1983-1986.
16. for the reaction with activated aromatic aldehydes, see:, S. Luo, H. Xu, L. Chen, J.-P. Cheng, Org. Lett. 2008, 10, 1775-1778.
17. N. Gathergood, K. Juhl, T. B. Poulsen, K. Thordrup, K. A. Jørgensen, Org. Biomol. Chem. 2004, 2, 1077-1085.
18. D. Enders, T. Gasperi, Chem. Commun. 2007, 88-90.
19. B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575.
20. K. Narasaka, F.-C. Pai, Tetrahedron 1984, 40, 2233-2238.
21. B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003-12004.
22. N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168-4178.
23. A. Dondoni, Org. Biomol. Chem. 2010, 8, 3366-3385.