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  Catalytic Asymmetric Synthesis of Thiols

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.

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 Creators:
Monaco, Mattia Ricardo1, Author              
Prévost, Sébastien1, Author
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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 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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Language(s): eng - English
 Dates: 2014-09-302014-11-262014-12-10
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja510069w
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 136 (49) Sequence Number: - Start / End Page: 16982 - 16985 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870