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Asymmetric Catalytic Cycloetherification Mediated by Bifunctional Organocatalysts

Keisuke Asano and Seijiro Matsubara*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan, Email:

K. Asano, S. Matsubara, J. Am. Chem. Soc., 2011, 133, 16711-16713.

DOI: 10.1021/ja207322d


Cinchona-alkaloid-thiourea-based bifunctional organocatalysts enable a straightforward asymmetric cycloetherification of ε-hydroxy-α,β-unsaturated ketones for the synthesis of tetrahydrofuran rings. This catalytic process represents a highly practical cycloetherification method that provides excellent enantioselectivities, even with low catalyst loadings at ambient temperature.

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Key Words

Tetrahydrofurans, Organocatalysis

ID: J48-Y2011-3030