Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

[Image: see text] The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catal...

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Autores principales: Boyce, Gregory R., Musolino, Stefania F., Yang, Jianing, Smith, Andrew D., Taylor, James E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552221/
https://www.ncbi.nlm.nih.gov/pubmed/36075004
http://dx.doi.org/10.1021/acs.joc.2c01602
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author Boyce, Gregory R.
Musolino, Stefania F.
Yang, Jianing
Smith, Andrew D.
Taylor, James E.
author_facet Boyce, Gregory R.
Musolino, Stefania F.
Yang, Jianing
Smith, Andrew D.
Taylor, James E.
author_sort Boyce, Gregory R.
collection PubMed
description [Image: see text] The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate.
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spelling pubmed-95522212022-10-12 Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols Boyce, Gregory R. Musolino, Stefania F. Yang, Jianing Smith, Andrew D. Taylor, James E. J Org Chem [Image: see text] The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate. American Chemical Society 2022-09-08 2022-10-07 /pmc/articles/PMC9552221/ /pubmed/36075004 http://dx.doi.org/10.1021/acs.joc.2c01602 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Boyce, Gregory R.
Musolino, Stefania F.
Yang, Jianing
Smith, Andrew D.
Taylor, James E.
Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols
title Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols
title_full Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols
title_fullStr Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols
title_full_unstemmed Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols
title_short Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols
title_sort arylboronic acid-catalyzed racemization of secondary and tertiary alcohols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552221/
https://www.ncbi.nlm.nih.gov/pubmed/36075004
http://dx.doi.org/10.1021/acs.joc.2c01602
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