Search results for "Intramolecular aza-Michael reaction"

showing 2 items of 2 documents

Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide

2011

The organocatalytic synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide is described. It involved, as the key step, an enantioselective intramolecular aza-Michael reaction (IMAMR) catalyzed by Jorgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.

MyrtineLupinineQuinolizidineStereochemistryOrganocatalysisOrganic ChemistryEnantioselective synthesisEpiquinamideBiochemistryEpiquinamideCatalysischemistry.chemical_compoundLupininechemistryOrganocatalysisIntramolecular forceDrug DiscoveryOrganic chemistryQuinolizidine alkaloidsIntramolecular aza-Michael reaction
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A new strategy for the synthesis of fluorinated 3,4-dihydropyrimidinones

2009

A new family of 3,4-dihydropyrimidinones (DHPMs) bearing fluorinated substituents at C6 have been prepared from gem-difluorinated nitriles, alkyl 3-butenoates and iso(thio)cyanates. This novel Biginelli-type process relies on the gamma-addition of the ester-derived enolate to fluorinated nitriles. A tandem nucleophilic addition aza-Michael reaction sequence completes the synthetic process. (C) 2009 Elsevier B.V. All rights reserved.

chemistry.chemical_classificationNucleophilic additionFluorinated nitrilesTandemChemistryOrganic ChemistryThio-BiochemistryInorganic ChemistryReaction sequenceMulticomponent reactionsEnvironmental ChemistryOrganic chemistryFluorinated dihydropyrimidinonesPhysical and Theoretical ChemistryAlkylIntramolecular aza-Michael reaction
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