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  Organocatalytic Asymmetric Hydrolysis of Epoxides

Monaco, M. R., Prévost, S., & List, B. (2014). Organocatalytic Asymmetric Hydrolysis of Epoxides. Angewandte Chemie International Edition, 53(31), 8142-8145. doi:10.1002/anie.201400170.

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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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Free keywords: biomimetic chemistry; carboxylysis; dihydroxylation; epoxides; organocatalysis
 Abstract: The hydrolytic ring opening of epoxides is an important biosynthetic transformation and is also applied industrially. We report the first organocatalytic variant of this reaction, exploiting our recently discovered activation of carboxylic acids with chiral phosphoric acids via heterodimerization. The methodology mimics the enzymatic mechanism, which involves an enzyme-bound carboxylate nucleophile. A newly designed phosphoric acid catalyst displays high stereocontrol in the desymmetrization of meso-epoxides. The methodology shows wide generality with cyclic, acylic, aromatic, and aliphatic substrates. We also apply our method in the first highly enantioselective anti-dihydroxylation of simple olefins.

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Language(s): eng - English
 Dates: 2014-01-072014-06-242014-07-28
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201400170
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 53 (31) Sequence Number: - Start / End Page: 8142 - 8145 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851