title: Asymmetric, organocatalytic, three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters.
abstract: An efficient and enantiocontrolled three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters is reported. Enantioenriched alpha-selenyl aldehydes, prepared in one step by asymmetric, organocatalytic alpha-selenylation of aldehydes, were directly subjected to a Wittig reaction followed by allylic selenide to selenoxide oxidation and final spontaneous [2,3]-sigmatropic rearrangement to yield the target compounds in 43-65% overall yield and in 94-97% ee.
authors.affiliation: Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
authors.forename: Lindsey C
authors.initials: LC
authors.lastname: Hess
authors.forename: Gary H
authors.initials: GH
authors.lastname: Posner
mesh_terms: D002384:Catalysis; D004952:Esters; D009930:Organic Chemicals / Q000737:chemistry*
chemical_list: D004952:Esters; D009930:Organic Chemicals