title: Asymmetric, organocatalytic, three-step synthesis of gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters.
abstract: Efficient and enantiocontrolled synthesis of gamma-hydroxy-alpha,beta-unsaturated sulfones and esters are reported through the reaction of enantioenriched alpha-selenyl aldehydes with EWG-stabilized carbanions and then a one-pot selenide oxidation, in situ epoxide formation, and final in situ epoxide opening.
authors.affiliation: Department of Chemistry, Johns Hopkins University, 3400 Charles Street, Baltimore, Maryland 21218, USA.
authors.forename: Kimberly S
authors.initials: KS
authors.lastname: Petersen
authors.forename: Gary H
authors.initials: GH
authors.lastname: Posner
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D008958:Models, Molecular; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D004952:Esters; D010880:Piperidines; D013450:Sulfones; C520251:alpha-conhydrine