title: Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones.
abstract: [reaction: see text] The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-delta-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted delta-lactones.
authors.affiliation: Department of Process Research, Merck Research Laboratories, Merck & Co., P.O. Box 2000, Rahway, New Jersey 07065, USA. jacqueline_smitrovich@merck.com
authors.forename: Jacqueline H
authors.initials: JH
authors.lastname: Smitrovich
authors.forename: Geneviève N
authors.initials: GN
authors.lastname: Boice
authors.forename: Chuanxing
authors.initials: C
authors.lastname: Qu
authors.forename: Lisa
authors.initials: L
authors.lastname: DiMichele
authors.forename: Todd D
authors.initials: TD
authors.lastname: Nelson
authors.forename: Mark A
authors.initials: MA
authors.lastname: Huffman
authors.forename: Jerry
authors.initials: J
authors.lastname: Murry
authors.forename: James
authors.initials: J
authors.lastname: McNamara
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Reider
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D004809:Ephedrine / Q000737:chemistry*; D007202:Indicators and Reagents; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D007783:Lactones; D004809:Ephedrine