Rapid fluorescent screening for bifunctional amine-acid catalysts: efficient syntheses of quaternary carbon-containing aldols under organocatalysis |
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Authors: | Mase Nobuyuki Tanaka Fujie Barbas Carlos F |
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Affiliation: | The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. |
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Abstract: | [reaction: see text] Direct catalytic aldol reactions of alpha,alpha-dialkylaldehyde donors and arylaldehyde acceptors have been performed using pyrrolidine-acetic acid bifunctional catalysts. This general and practical amine-acid combination was identified by screening catalysts using a new fluorescent detection system for carbon-carbon bond formation. Using 0.05 equiv of pyrrolidine and 0.25 equiv of acetic acid as catalyst, we obtained alpha,alpha-dialkylaldol product in 96% yield after 2 h at ambient temperature. Proline was a poor catalyst of this reaction. |
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