Catalytic Asymmetric Cycloadditions between Aldehydes and Enolizable Anhydrides: cis-Selective Dihydroisocoumarin Formation

In the presence of a trityl-substituted cinchona alkaloid-based catalyst, homophthalic, aryl succinic, and glutaconic anhydride derivatives reacted with aromatic and aliphatic aldehydes to produce cis-lactones in up to 90:10 dr and 99% ee. A DFT study has shown how the catalyst is uniquely able to b...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-12, Vol.83 (24), p.15499-15511
Main Authors: Aiello, Maria Luisa, Farid, Umar, Trujillo, Cristina, Twamley, Brendan, Connon, Stephen J
Format: Article
Language:English
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Summary:In the presence of a trityl-substituted cinchona alkaloid-based catalyst, homophthalic, aryl succinic, and glutaconic anhydride derivatives reacted with aromatic and aliphatic aldehydes to produce cis-lactones in up to 90:10 dr and 99% ee. A DFT study has shown how the catalyst is uniquely able to bring about the opposite sense of diastereocontrol to that usually observed.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02332