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. 2021 Apr 8:17:800-804.
doi: 10.3762/bjoc.17.68. eCollection 2021.

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

David Weinzierl  1 , Mario Waser  1
Affiliations

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

David Weinzierl et al. Beilstein J Org Chem. .

Abstract

We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of a 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: acylation; kinetic resolution; nucleophilic catalysis; paracyclophanes; planar chirality.

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Figures

Scheme 1
Scheme 1
Overview about established methods to access enantioenriched 2 and the herein investigated kinetic resolution (KR) with chiral isothiourea (ITU) catalysts.
Scheme 2
Scheme 2
Use of alternative acylating agents 4 for the kinetic resolution of rac-2.
See this image and copyright information in PMC

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