PubAg

Main content area

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

Author:
Aiello, Maria Luisa, Farid, Umar, Trujillo, Cristina, Twamley, Brendan, Connon, Stephen J.
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15499-15511
ISSN:
1520-6904
Subject:
Cinchona, aldehydes, anhydrides, catalysts, chemical structure, cycloaddition reactions, isocoumarins, organic chemistry
Abstract:
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.
Agid:
6266393