Cinchona Derivatives as Bifunctional Organocatalysts for the Direct Asymmetric Nitroaldol (Henry) Reaction

Tommaso Marcelli; Richard N. S. van der Haas; Jan H. van Maarseveen; Henk Hiemstra

doi:10.1055/s-2005-918935

LETTER

Cinchona Derivatives as Bifunctional Organocatalysts for the Direct Asymmetric Nitroaldol (Henry) Reaction

Tommaso Marcelli, Richard N. S. van der Haas, Jan H. van Maarseveen, Henk Hiemstra*
Van’t Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
Fax: +31(20)5255670; e-Mail: hiemstra@science.uva.nl;

Abstract

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Abstract

Bifunctional Cinchona derivatives are asymmetric catalysts for the nitroaldol reaction. Enantiomeric excesses up to 45% have been achieved with activated aromatic aldehydes.

Key words

asymmetric organocatalysis - bifunctional catalysis - Cinchona alkaloids - nitroaldol reaction - nitroalcohols

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References

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In ref. 5 the ee reported for 1a is 81% in the preliminary studies and 78% for a preparative run after work-up and chromatography. This corresponds approximately to the same loss of optical purity we experienced.