Issue 4, 2022

Organocatalytic atroposelective construction of axially chiral nonsymmetric biaryltriols and their applications in asymmetric synthesis and heavy metal ion detection

Abstract

An organocatalytic methodology toward the atroposelective construction of axially chiral nonsymmetric biaryltriols has been successfully developed. A quinine-derived thiourea-catalyzed intramolecular reaction using VQM (vinylidene ortho-quinone methides) intermediates enabled efficient access to a class of axially chiral nonsymmetric biaryltriols with up to 98% yield and 99% ee. This strategy allows the convenient construction of atropoisomeric compounds with broad functional group tolerance under mild conditions. The new biaryltriols can be applied as chiral ligands for the enantioselective preparation of chiral sec-alcohols, or as organocatalysts for the asymmetric Petasis reaction to give the corresponding adducts with up to 95% yield and 83% ee under unmodified reaction conditions. In addition, axially chiral nonsymmetric biaryltriols have demonstrated potential utility as selective fluorescent sensors toward Ru3+ ions.

Graphical abstract: Organocatalytic atroposelective construction of axially chiral nonsymmetric biaryltriols and their applications in asymmetric synthesis and heavy metal ion detection

Associated articles

Supplementary files

Article information

Article type
Research Article
Submitted
06 des. 2021
Accepted
12 jan. 2022
First published
14 jan. 2022

Org. Chem. Front., 2022,9, 923-928

Organocatalytic atroposelective construction of axially chiral nonsymmetric biaryltriols and their applications in asymmetric synthesis and heavy metal ion detection

S. Jia, W. Qin, P. Wang and H. Yan, Org. Chem. Front., 2022, 9, 923 DOI: 10.1039/D1QO01821C

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