Direct catalytic asymmetric cross-aldol reactions in ionic liquid media

Tetrahedron Letters

Volumn 45, Issue 20, 2004, Pages 3949-3952

  Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1 N BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 3 HYDROXYALDEHYDE; ALDEHYDE; FLUOROPHOSPHATE; ION; PROLINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; ENANTIOSELECTIVITY; LIQUID; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 1942467938     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.080     Document Type: Article

References (32)

1. Rogers R.D., Seddon K.R. Science. 303:2003;792.
2. Seddon R. Chem. Commun. 2001;2399.
3. Dalko P.I., Moisan L. Angew. Chem., Int. Ed. 40:2001;3726.
4. List B. Tetrahedron. 58:2002;5573.
5. Jarvo E.R., Miller S.J. Tetrahedron. 58:2002;2481.
6. Duthaler R.O. Angew. Chem., Int. Ed. 42:2003;975.
7. Gijsen H.J.M., Qiao L., Fitz W., Wong C.-H. Chem. Rev. 96:1996;443.
8. Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. 39:2000;1352.
9. Córdova A., Notz W., Barbas C.F. III J. Org. Chem. 67:2002;301.
10. Córdova A. Synlett. 2003;1651.
11. Córdova A., Notz W., Barbas C.F. III Chem. Commun. 2002;3034.
12. Córdova A. Acc. Chem. Res. 37:2004;102.
13. Córdova A., Watanabe S.-I., Tanaka F., Notz W., Barbas C.F. III J. Am. Chem. Soc. 124:2002;1866.
14. Córdova A., Barbas C.F. III Tetrahedron Lett. 43:2002;7749.
15. Córdova A., Barbas C.F. III Tetrahedron Lett. 44:2003;1923.
16. Chowdari N.S., Ramachary D.B., Córdova A., Barbas C.F. III Tetrahedron Lett. 43:2002;9591.
17. Bøgevig A., Sundén H., Córdova A. Angew. Chem., Int. Ed. 43:2004;1109.
18. Northrup A.B., MacMillan D.W.C. J. Am. Chem. Soc. 124:2002;6798.
19. Bøgevig A., Juhl K., Kumaragurubaran N., Jørgensen K.A. Chem. Commun. 2002;620.
20. For other proline-catalyzed asymmetric reactions with aldehydes see: Bøgevig A., Juhl K., Kumaragurubaran N., Zhuang W., Jørgensen K.A. Angew. Chem., Int. Ed. 41:2002;1790.
21. List B. J. Am. Chem. Soc. 124:2002;5656.
22. Kumaragurubaran N., Juhl K., Zhuang W., Bøgevig A., Jørgensen K.A. J. Am. Chem. Soc. 124:2002;6254.
23. Pidathala C., Hoang L., Vignola N., List B. Angew. Chem., Int. Ed. 42:2003;2785.
24. 4. It has also been successfully used in aldol reactions with unmodified ketones see: Kotrusz P., Kmentová I., Gotov B., Toma S., Solcániová E. Chem. Commun. 2002;2510.
25. Loh T.-P., Feng L.-C., Yang H.-Y., Yang J.-Y. Tetrahedron Lett. 43:2002;8741.
26. The cross-aldol adducts were reduced quantitatively and the corresponding anti-1,3-diols converted to the 2,2-dimethylpropane-1,3-diols according to Ref. 5 and the ee determined by chiral-phase GC analysis. The racemic 2,2-dimethylpropane-1,3-diols derived by racemic proline-catalysis were checked as GC standards.
27. 6 to DMF ratio of 1.5:1. The combined organic extracts were concentrated and the crude product purified by silica-gel column chromatography (pentane/EtOAc 3:1) affording β-hydroxy aldehyde 2 in 76% yield with dr > 19:1 and > 99% ee. All the structural and spectroscopical data were identical to the literature. See: Ref. 5 and Mahrwald R., Costrisella B., Guendogan B. Synthesis. 1998;26.
28. Khosla C., Harbury P.B. Nature. 409:2001;247.
29. Kinoshita K., Willard P.G., Khosla C., Cane D.E. J. Am. Chem. Soc. 123:2001;2495. and references cited therein.
30. Gijsen H.J.M., Wong C.-H. J. Am. Chem. Soc. 117:1995;2947.
31. 3). The ee of δ-lactones 7a and 7b was determined by esterification of the alcohol group with 3,5-dinitro-benzoyl chloride according to Ref. [4h] and subsequent chiral-phase HPLC-analysis of the corresponding 3,5-dinitrobenzoate ester.
32. 3).