An Efficient Organocatalytic Method for Highly Enantioselective Michael Addition of Malonates to Enones Catalyzed by Readily Accessible Primary Amine-Thiourea

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 th...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 16; pp. 4222 - 4225
Main Authors Dudziński, Krzysztof, Pakulska, Anna M, Kwiatkowski, Piotr
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.08.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
ALPHA,BETA-UNSATURATED KETONES
AROMATIC KETONES
DIRECT CONJUGATE ADDITION
ESTERS
NITROALKANES
DERIVATIVES
(-)-STRYCHNINE
ALPHA,ALPHA-DISUBSTITUTED ALDEHYDES
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/ol3019055