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Catalytic Asymmetric Synthesis of Thiols

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Monaco,  Mattia Ricardo
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Prévost,  Sébastien
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Monaco, M. R., Prévost, S., & List, B. (2014). Catalytic Asymmetric Synthesis of Thiols. Journal of the American Chemical Society, 136(49), 16982-16985. doi:10.1021/ja510069w.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-93FA-9
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.