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Updated: Apr 19, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Catalytic asymmetric synthesis of thiols
Mattia Riccardo Monaco1, Sébastien Prévost, Benjamin List
1Max-Planck-Institut für Kohlenforschung , Kaiser-Wilhelm Platz 1, 45470 Mülheim an der Ruhr, Germany.
Abstract:
The synthesis of enantiopure thiols is of significant interest for industrial and academic applications. However, direct asymmetric approaches to free thiols have previously been unknown. Here we describe a novel organocascade that is catalyzed by a confined chiral phosphoric acid and furnishes O-protected β-hydroxythiols with excellent enantioselectivities. The method relies on an asymmetric thiocarboxylysis of meso-epoxides, followed by an intramolecular trans-esterification reaction. By varying the reaction conditions, the intermediate thioesters can also be obtained chemoselectively and enantioselectively.
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