Cinchona Alkaloid-Silyl Ether Derivatives as Organocatalysts for Asymmetric “Interrupted” Feist-Bénary Reaction

Article Preview

Abstract:

Four cinchona alkaloid-silyl ether derivatives have been used to catalyze the asymmetric “interrupted” Feist-Bénary reaction of ethyl bromopyruvate/substituted bromo-ketoesters and 1,3-Cyclohexadione. The corresponding hydroxydihydrofurans have been obtained in excellent yields (85-96%) with high enantiomeric excess (ee) values of up to 90%.

You might also be interested in these eBooks

Info:

Periodical:

Advanced Materials Research (Volumes 864-867)

Pages:

456-459

Citation:

Online since:

December 2013

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2014 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

* - Corresponding Author

[1] M.A. Calter, R.J. Lachicotte, Rapid synthesis of the 7-deoxy zaragozic acid core, Org. Lett. 4(2002) 209-212.

DOI: 10.1021/ol0169980

Google Scholar

[2] M.A. Calter, C. Zhu, Scope and diastereoselectivity of the Interrupted, Feist-Bénary reaction, Org. Lett. 4(2002) 205-208.

DOI: 10.1021/ol0169978

Google Scholar

[3] I.J. Dunlop, C.D. Hurd, Base-Catalyzed condensation of α-halogenated ketones with β-keto esters, J. Org. Chem. 15(1950)1160-1164.

DOI: 10.1021/jo01152a006

Google Scholar

[4] I.J. Canton, W. Cocke, T.B.H. MeMurry, Reactions of some dicarbonyl compounds, Tetrahedron 15(1961) 45-52.

Google Scholar

[5] M.A. Calter, R.M. Phillips, C.J. Flaschenriem, Catalytic asymmetric"Interrupted"Feist-Bénary reaction. J. Am. Chem. Soc. 127(2005) 14566-14567.

DOI: 10.1021/ja055752d

Google Scholar

[6] Y. Jin, X.Y. Liu, L.L. Jing, W. He, X.L. Sun, S.Y. Zhang, Investigation on 1, 4-dichlorophthalazine-derivetized Cinchona alkaloids- catalyzed Asymmetric interrupted, Feist-Bénary Reaction, Chirality 19(2007) 386-390.

DOI: 10.1002/chir.20394

Google Scholar

[7] Y. Jin, Z.J. Yao, P. Liu, R. Jiang, S.Y. Zhang, Investigation on 3, 6-dichloropyridazine- derivetized Cinchona alkaloids- catalyzed Asymmetric interrupted, Feist-Bénary Reaction, Chin. J. Org. Chem. 28(2008) 94-98.

DOI: 10.1002/chir.20394

Google Scholar

[8] J. Okanya, R. Hoffman, M.C. Johnson, Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3- Bromo -2-ketoesters, J. Org. Chem. 67(2002) 1102-1108.

DOI: 10.1021/jo010630z

Google Scholar

[9] T.Y. Zhang, W. He, X.Y. Zhao, Y. Jin, Asymmetric oxaziridination catalyzed by cinchona alkaloid derivatives containing sulfide. Tetrahedron 69(2013) 7416-7422.

DOI: 10.1016/j.tet.2013.06.061

Google Scholar