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

Maria Luisa Aiello, Umar Farid, Cristina Trujillo, Brendan Twamley, Stephen J. Connon*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)15499-15511
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number24
Early online date21 Nov 2018
DOIs
Publication statusPublished - 21 Dec 2018

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