Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols.

Angew Chem Int Ed Engl

Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Poly-technique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne, 1015, Switzerland.

Published: October 2021

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols which are important synthetic intermediates and end products for many industries. Driven by visible light only, this method is based on sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation. The combination of a heterogeneous dehydrogenation photocatalyst and a chiral molecular hydrogenation catalyst is essential to ensure two distinct pathways for the forward and reverse reactions. These reactions convert a large number of racemic aryl alkyl alcohols into their enantiomerically enriched forms in good yields and enantioselectivities.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8519112PMC
http://dx.doi.org/10.1002/anie.202107570DOI Listing

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