Asymmetric catalysis, CIII: EnantioselectiveMichael addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1996-10

AUTHORS

H. Brunner, B. Kimel

ABSTRACT

Optically activeMichael adducts were synthesized by addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes. Good chemical yields were obtained for nitroalkenes stabilized by an aromatic substituent without any further substituents at the double bond. Acetylacetone and methyl-2,3-dihydro-1-oxo-1H-indene-2-carboxylate were used asMichael donors and four cinchona alkaloids as chiral base catalysts. Enantiomeric excess determinations were performed by1H NMR spectroscopy in the presence of thePirkle alcohol and by HPLC on chiral stationary phases. A correlation between the relative configuration of the prevailing isomer of theMichael adduct and the catalysts was established. More... »

PAGES

1063-1072

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf00807579

DOI

http://dx.doi.org/10.1007/bf00807579

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1047397840


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