title: α-Chloro-β,γ-ethylenic esters: enantiocontrolled synthesis and substitutions.
abstract: Chiral nonracemic γ-seleno-α,β-ethylenic esters, when treated with sulfuryl chloride and ethyl vinyl ether in hexanes, produced α-chloro-β,γ-ethylenic esters in 65-75% yields, with ee values of 95-97%, and with 1,3-syn transfer of chirality. Reaction of these allylic chloride electrophiles with methylcuprate and with sodium azide nucleophiles afforded exclusively γ-substituted-α,β-ethylenic esters with faithful anti-transfer of chirality on multigram scale.
authors.affiliation: Department of Chemistry, The Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
authors.forename: Douglas T
authors.initials: DT
authors.lastname: Genna
authors.forename: Christopher P
authors.initials: CP
authors.lastname: Hencken
authors.forename: Maxime A
authors.initials: MA
authors.lastname: Siegler
authors.forename: Gary H
authors.initials: GH
authors.lastname: Posner