title: An asymmetric Michael addition of α,α-disubstituted aldehydes to maleimides leading to a one-pot enantioselective synthesis of lactones catalyzed by amino acids.
abstract: A cheap and fast construction of both enantiomers of substituted succinimides is reported. α- or β-amino acids, such as β-phenylalanine and α-tert-butyl aspartate, were found to be efficient organocatalysts for the reaction between α,α-disubstituted aldehydes and maleimides. Products containing contiguous quaternary-tertiary stereogenic centers are obtained in high to quantitative yields and excellent selectivities utilizing low catalyst loadings (0.5-3.5%). Finally, a one-pot efficient asymmetric synthesis of lactones is described.
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry, University of Athens , Panepistimiopolis 15771, Athens, Greece.
authors.forename: Christoforos G
authors.initials: CG
authors.lastname: Kokotos
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D010649:Phenylalanine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D007783:Lactones; D008301:Maleimides; C000588527:alpha-tert-butyl aspartate; D001224:Aspartic Acid; D010649:Phenylalanine