Abstract
A series of secondary amine-thiourea catalysts 1a-1d derived from L-proline and chiral diamine were prepared and successfully applied to the Michael addition of acetone to trans-nitroalkenes in excellent yields (up to 99%) and enantioselectivities (44-91% ee).
Highlights
Michael addition is one of the most important reactions in carbon-carbon bond formation.Michael reaction involved trans-nitroalkenes and ketones is a convenient approach to γ-nitroketones which are valuable building blocks in organic synthesis and could be readily converted to commercially important pharmaceutical products via γ-aminobutyric acids.[1,2] Over the past years, various efficient chiral organocatalysts have been developed for the enantioselective Michael addition of aldehydes,[3] ketones[4] and 1,3-dicarbonyl compounds[5] to nitroalkenes
Various efficient chiral organocatalysts have been developed for the enantioselective Michael addition of aldehydes,[3] ketones[4] and 1,3-dicarbonyl compounds[5] to nitroalkenes
Excellent results have been achieved by these systems, few excellent protocols of asymmetric Michael addition of acetone to nitroalkenes were reported.[9]
Summary
Michael addition is one of the most important reactions in carbon-carbon bond formation.Michael reaction involved trans-nitroalkenes and ketones is a convenient approach to γ-nitroketones which are valuable building blocks in organic synthesis and could be readily converted to commercially important pharmaceutical products via γ-aminobutyric acids.[1,2] Over the past years, various efficient chiral organocatalysts have been developed for the enantioselective Michael addition of aldehydes,[3] ketones[4] and 1,3-dicarbonyl compounds[5] to nitroalkenes.
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