title: Enantioselective synthesis of tertiary α-chloro esters by non-covalent catalysis.
abstract: We report an enantioselective approach to tertiary α-chloro esters through the reaction of silyl ketene acetals andN-chlorosuccinimide. The reaction is promoted by a chiral squaramide catalyst, which is proposed to engage both reagents exclusively through non-covalent interactions. Application of the tertiary chloride products in stereospecific substitution reactions is demonstrated.
authors.affiliation: Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
authors.forename: Richard Y
authors.initials: RY
authors.lastname: Liu
authors.affiliation: Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Wasa
authors.affiliation: Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
keywords: Asymmetric catalysis; Chlorination; Hydrogen bonding; Non-covalent interations; Organocatalysis