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Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically-Formed Chiral Auxiliary
preprintsubmitted on 24.08.2020, 14:59 and posted on 25.08.2020, 09:30 by Luca Buzzetti, Mikus Purins, Phillip D. G. Greenwood, Jerome Waser
Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited either in terms of efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity of chemical reactions. Asymmetric catalysis is used to install a transient chiral auxiliary starting from achiral precursors, which then directs diastereoselective reactions. We apply this strategy to a palladium-catalyzed carboetherification/hydrogenation sequence on propargylic amines, providing fast access to enantioenriched chiral amino alcohols, important building blocks for medicinal chemistry and drug discovery. All stereoisomers of the product could be accessed by the choice of ligand and substituent on the propargylic amine, leading to a stereodivergent process.