Issue 80, 2014

Asymmetric Michael/hemiketalization of 5-hydroxy-2-methyl-4H-pyran-4-one to β,γ-unsaturated α-ketoesters catalyzed by a bifunctional rosin–indane amine thiourea catalyst

Abstract

A highly efficient asymmetric cascade reaction namely Michael-hemiketalization of 5-hydroxy-2-methyl-4H-pyran-4one to β,γ-unsaturated α-ketoesters has been developed using a chiral bifunctional rosin–indane amine thiourea catalyst. The products are obtained in excellent yields with a high degree of enantiomeric excess (up to 99% ee), in a short reaction time with low catalyst loading of 2.5 mol%.

Graphical abstract: Asymmetric Michael/hemiketalization of 5-hydroxy-2-methyl-4H-pyran-4-one to β,γ-unsaturated α-ketoesters catalyzed by a bifunctional rosin–indane amine thiourea catalyst

Supplementary files

Article information

Article type
Paper
Submitted
06 Aug 2014
Accepted
21 Aug 2014
First published
28 Aug 2014

RSC Adv., 2014,4, 42299-42307

Author version available

Asymmetric Michael/hemiketalization of 5-hydroxy-2-methyl-4H-pyran-4-one to β,γ-unsaturated α-ketoesters catalyzed by a bifunctional rosin–indane amine thiourea catalyst

B. V. S. Reddy, M. Swain, S. M. Reddy, J. S. Yadav and B. Sridhar, RSC Adv., 2014, 4, 42299 DOI: 10.1039/C4RA06938B

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