An efficient organocatalytic method for highly enantioselective Michael addition of malonates to enones catalyzed by readily accessible primary amine-thiourea |
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Authors: | Krzysztof Dudziński Anna M Pakulska Piotr Kwiatkowski |
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Affiliation: | Faculty of Chemistry, University of Warsaw , Pasteura 1, 02-093 Warsaw, Poland. |
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Abstract: | A practical and highly enantioselective Michael addition of malonates to enones catalyzed by simple and readily available bifunctional primary amine-thiourea derived from 1,2-diaminocyclohexane is reported. The addition of weak acids and elevated temperature (ca. 50 °C) improved the efficiency of the Michael reaction. This approach enables the efficient synthesis of 1,5-ketoesters with good yields, excellent enantioselectivities (up to 99% ee), and low loading (0.5-5 mol %) of simple chiral primary amine-thiourea catalysts, and is applicable in multigram scale synthesis. |
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