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Catalytic Asymmetric Cycloadditions between Aldehydes and Enolizable Anhydrides: cis-Selective Dihydroisocoumarin Formation
- Aiello, Maria Luisa, Farid, Umar, Trujillo, Cristina, Twamley, Brendan, Connon, Stephen J.
- Journal of organic chemistry 2018 v.83 no.24 pp. 15499-15511
- Cinchona, aldehydes, anhydrides, catalysts, chemical structure, cycloaddition reactions, isocoumarins, organic chemistry
- 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.