期刊
SCIENCE
卷 351, 期 6276, 页码 949-952出版社
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aae0010
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资金
- Max Planck Society
- Stiftung Industrieforschung
- Fonds der Chemischen Industrie
- European Research Council
- Deutsche Forschungsgemeinschaft [EXC 1069]
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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