Applications of Optically Pure Biphenyloxycyclohexanols in Deracemization of α-Substituted Aryloxypropanoic Acids by Dynamic Kinetic Resolution

Dedication

Dedicated to Prof. S. Chandrasekaran on his 80^th birthday and in recognition of his immense contributions to the field of organic synthesis.

Abstract

Two derivatives of chiral trans-2-biphenyloxycyclohexanol were screened as chiral auxiliaries for the α-alkylation of aryloxypropanoic acids to obtain enriched enantiomers. The chiral auxiliary controls the enantioselective formation of α-aryloxypropanoic acids by dynamic kinetic resolution. The 2-phenylphenoxy derivative was found to be more effective in controlling chirality in the product as compared to its 4-phenylphenoxy isomer. Formation of the major isomer is supported by the calculation of their relative energies by computational analysis, using Gaussian 16.0 B3LYP/6-31+G(d) as a basis set.

Keywords

trans-2-Aryloxycyclohexanol - Dynamic kinetic resolution - α-Substituted propanoic acids - Asymmetric synthesis

Publikationsverlauf

Eingereicht: 09. Juni 2025

Angenommen nach Revision: 28. Juli 2025

Artikel online veröffentlicht:
27. November 2025

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