Chiral Isothiourea-Catalyzed Kinetic Resolution of 4-Hydroxy[2.2]paracyclophane

Submitting author affiliation:
Johannes Kepler University Linz, Linz, Austria

Beilstein Arch. 2021, 202114.

Published 25 Feb 2021

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We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of an chiral isothiourea-catalyzed acylation with isobutyric anhydride. This protocol allows for a reasonable synthetically useful s-factor of 20 and provides a novel entry to obtain this interesting planar chiral motive in an enantioenriched manner.

Keywords: Kinetic resolution; paracyclophanes; planar chirality; nucleophilic catalysis; acylation

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Weinzierl, D.; Waser, M. Beilstein Arch. 2021, 202114. doi:10.3762/bxiv.2021.14.v1

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