title: Stereoselective Synthesis of α-Fluoro-γ-nitro Thioesters under Organocatalytic Conditions.
abstract: Fluorinated monothiomalonates (F-MTMs) were used as building blocks for the stereoselective synthesis of organofluorine compounds. We present conjugate addition reactions between F-MTMs with nitroolefins that proceed under mild organocatalytic conditions and provide access to α-fluoro-γ-nitro thioesters with adjacent tetrasubstituted and tertiary stereogenic centers. Only 1 mol % of a cinchona alkaloid-urea catalyst is necessary to obtain the addition products in excellent yields and stereoselectivities. The methodology allowed for the straightforward synthesis of a fluorinated analogue of the PAR-2 agonist AC-264613.
authors.affiliation: Laboratory of Organic Chemistry, ETH Zurich , Vladimir-Prelog-Weg 3, CH-8093 Zurich, Switzerland.
authors.forename: Elena
authors.initials: E
authors.lastname: Cosimi
authors.affiliation: Laboratory of Organic Chemistry, ETH Zurich , Vladimir-Prelog-Weg 3, CH-8093 Zurich, Switzerland.
authors.forename: Jakub
authors.initials: J
authors.lastname: Saadi
authors.affiliation: Laboratory of Organic Chemistry, ETH Zurich , Vladimir-Prelog-Weg 3, CH-8093 Zurich, Switzerland.
authors.forename: Helma
authors.initials: H
authors.lastname: Wennemers