Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C–H Bond Formation
Jérôme Waser reports on the counterintuitive use of an aryl iodide additive in C–H bond forming reactions.
Stereodefined aryl-substituted β-amino alcohols are important compounds in organic chemistry and find extensive use as ligands or building blocks in asymmetric synthesis, as well as in drug discovery. The development of stereocontrolled and efficient and catalytic synthetic methods to access these compounds remains a vibrant area of research in medicinal and bioorganic chemistry. The group of Professor Jérôme Waser (Ecole Polytechnique Fédérale de Lausanne, Switzerland) has a long-standing interest in difunctionalization reactions of unsaturated systems by exploiting molecular tethers to enhance reactivity and control selectivity. Recently, they reported a tethered asymmetric carboetherification of propargylic amines, aryl iodides and a trifluoroacetaldehyde-derived molecular tether to generate tetra-substituted olefins containing a rigid oxazolidine ring.