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

David Weinzierl; Mario Waser

doi:10.3762/bxiv.2021.14.v1

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

David Weinzierl and
Mario Waser

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

Beilstein Arch. 2021, 202114. https://doi.org/10.3762/bxiv.2021.14.v1

Published 25 Feb 2021

Preprint

Read the peer-reviewed version of this preprint: https://doi.org/10.3762/bjoc.17.68

Abstract

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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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)

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

Read the peer-reviewed version of this preprint: https://doi.org/10.3762/bjoc.17.68

Abstract

Supporting Information

How to Cite

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