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submitted on 24.08.2020 and posted on 25.08.2020by 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.