Enantioseparation of -Stereogenic 1-Adamantyl Arylthiophosphonates and Their Stereospecific Transformation to 1-Adamantyl Aryl--phosphinates

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2023 Feb 25

PMID 36838571

Authors

Bence Varga

Levente Buna

Daniella Vincze

Tamas Holczbauer

Bela Matravolgyi

Elemer Fogassy

Gyorgy Keglevich

Peter Bagi

Affiliations

Soon will be listed here.

Abstract

A focused library of 1-adamantyl arylthiophosphonates was prepared in racemic form. An enantioseparation method was developed for -stereogenic thiophosphonates using ()-1-phenylethylamine as the resolving agent. Under optimized conditions, three out of the five arylthiophosphonates were prepared in enantiopure form ( > 99%). The subsequent desulfurization of optically active arylthiophosphonates gave the corresponding -phosphinates without significant erosion of enantiomeric purity ( = 95-98%). Hence, this reaction sequence can be considered an alternative method for the preparation of 1-adamantyl aryl--phopshinates. The absolute configuration of the ()-1-adamantyl phenylphosphonothioic acid was assigned using single-crystal XRD and it allowed the confirmation that the removal of the P = S group proceeds with retention of configuration. The organocatalytic applicability of ()-1-adamantyl phenylphosphonothioic acid was also evaluated as a -stereogenic acid.

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