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  • Title: Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid.
    Author: Gatzenmeier T, van Gemmeren M, Xie Y, Höfler D, Leutzsch M, List B.
    Journal: Science; 2016 Feb 26; 351(6276):949-52. PubMed ID: 26917765.
    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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