title: Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution.
abstract: In a previous study it was shown that the enantioselective α-fluorination of racemic α-chloroaldehydes with a chiral organocatalyst yielded the corresponding α-chloro-α-fluoroaldehydes with high enantioselectivity. It was also revealed that kinetic resolution of the starting aldehydes was involved in this asymmetric fluorination. This paper describes the determination of the absolute stereochemistry of a resulting α-chloro-α-fluoroaldehyde. Some information about the substrate scope and a possible reaction mechanism are also described which shed more light on the nature of this asymmetric fluorination reaction.
authors.affiliation: Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
authors.forename: Kazutaka
authors.initials: K
authors.lastname: Shibatomi
authors.affiliation: Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Okimi
authors.affiliation: Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Abe
authors.affiliation: Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
authors.forename: Akira
authors.initials: A
authors.lastname: Narayama
authors.affiliation: Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
authors.forename: Nami
authors.initials: N
authors.lastname: Nakamura
authors.affiliation: Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
authors.forename: Seiji
authors.initials: S
authors.lastname: Iwasa
keywords: asymmetric catalysis; chlorination; fluorination; organo-fluorine; organocatalyst; α-branched aldehyde