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  Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid

Gatzenmeier, T., van Gemmeren, M., Xie, Y., Höfler, D., Leutzsch, M., & List, B. (2016). Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid. Science, 351(6276), 949-952. doi:10.1126/science.aae0010.

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 Creators:
Gatzenmeier, Tim1, Author              
van Gemmeren, Manuel1, Author              
Xie, Youwei1, Author              
Höfler, Denis1, Author              
Leutzsch, Markus1, Author              
List, Benjamin1, Author              
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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_persistent22              

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 Abstract: Silylium ion equivalents have shown promise as Lewis acid catalysts for a range of important C-C bond-forming reactions. Here we describe chiral C-H acids that upon in situ silylation, generate silylium-carbanion pairs, which are extremely active Lewis acid catalysts for enantioselective Diels-Alder reactions of cinnamates with cyclopentadiene. Enantiomeric ratios of up to 97: 3 and diastereomeric ratios of more than 20: 1 are observed across a diverse set of substitution patterns with 1 mole percent (mol %) of C-H acid catalyst and 10 mol % of a silylating reagent. The results show promise for broad applications of such C-H acid-derived silylium ion equivalents in asymmetric Lewis acid catalysis.

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Language(s): eng - English
 Dates: 2016-02-26
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1126/science.aae0010
 Degree: -

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Title: Science
  Abbreviation : Science
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Association for the Advancement of Science
Pages: - Volume / Issue: 351 (6276) Sequence Number: - Start / End Page: 949 - 952 Identifier: ISSN: 0036-8075
CoNE: https://pure.mpg.de/cone/journals/resource/991042748276600_1