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Journal Article

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

MPS-Authors
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Gatzenmeier,  Tim
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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van Gemmeren,  Manuel
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons191820

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

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

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Leutzsch,  Markus
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

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.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002A-0FC8-1
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.