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Michael addition of carbonyl compounds to nitroolefins under the catalysis of new pyrrolidine-based bifunctional organocatalysts

AuthorsCastán, Alejandro; Badorrey, Ramón ; Gálvez, José A. ; López-Ram-de-Víu, Pilar ; Díaz de Villegas, María D.
Issue Date2018
PublisherRoyal Society of Chemistry (UK)
CitationOrganic and Biomolecular Chemistry 16(6): 924-935 (2018)
AbstractNovel bifunctional pyrrolidine-based organocatalysts for the asymmetric Michael addition of carbonyl compounds to nitroolefins have been synthesised from homoallylamines, which are easily obtained from (R)-glyceraldehyde as a chiral precursor. Under optimal reaction conditions, these bifunctional organocatalysts showed a high catalytic efficiency (almost quantitative yield in most cases) and stereoselectivity in the Michael addition reactions of a variety of aldehydes (up to 98 : 2 dr and 97% ee) and ketones (up to 98 : 2 dr and 99% ee) to nitroolefins.
Publisher version (URL)https://doi.org/10.1039/C7OB02798B
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