title: Gold(I)-catalyzed, stereocontrolled enamide synthesis from primary amides and propargyl aldehydes using a tandem strategy.
abstract: A novel strategy for enamide synthesis from primary amides and propargyl aldehydes via Au(I)-catalyzed tandem amide addition and Meyer-Schuster rearrangement is described. In situ generated hemiaminals were successfully converted to the desired products under the optimized conditions. Enamide stereochemistry was controlled simply by changing solvents and adding a catalytic amount of acid. The developed synthetic strategy provides a new method to synthesize various β-substituted α,β-unsaturated carbonyl compounds.
authors.affiliation: Center for Nanoparticle Research, Institute for Basic Science (IBS), Gwanak-gu, Seoul 151-742, Republic of Korea.|Department of Chemistry, College of Natural Sciences, Seoul National University, 599 Gwanak-ro, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Sang Min
authors.initials: SM
authors.lastname: Kim
authors.affiliation: Center for Nanoparticle Research, Institute for Basic Science (IBS), Gwanak-gu, Seoul 151-742, Republic of Korea.|Department of Chemistry, College of Natural Sciences, Seoul National University, 599 Gwanak-ro, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Dabon
authors.initials: D
authors.lastname: Lee
authors.affiliation: Center for Nanoparticle Research, Institute for Basic Science (IBS), Gwanak-gu, Seoul 151-742, Republic of Korea.|Department of Chemistry, College of Natural Sciences, Seoul National University, 599 Gwanak-ro, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Soon Hyeok
authors.initials: SH
authors.lastname: Hong
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000577:Amides; D007659:Ketones; D006046:Gold