Issue 56, 2023

Asymmetric iminium ion-catalyzed conjugate addition of 2-hydroxycinnamaldehydes and 2-oxocarboxylic esters: synthesis of chiral polysubstituted bridged bicyclic ketals

Abstract

A highly regio-, chemo-, and stereoselective cascade process initiated by enantioselective iminium-catalyzed conjugate addition of 2-hydroxycinnamaldehydes and 2-oxocarboxylic esters is presented. Normal cinnamaldehydes are not reactive under the same reaction conditions. Bridged bicyclic ketals rather than acetals bearing stereocenters on both the bridge carbon and bridgehead ketal carbon are synthesized.

Graphical abstract: Asymmetric iminium ion-catalyzed conjugate addition of 2-hydroxycinnamaldehydes and 2-oxocarboxylic esters: synthesis of chiral polysubstituted bridged bicyclic ketals

Supplementary files

Article information

Article type
Communication
Submitted
07 Jun 2023
Accepted
16 Jun 2023
First published
16 Jun 2023

Chem. Commun., 2023,59, 8711-8714

Asymmetric iminium ion-catalyzed conjugate addition of 2-hydroxycinnamaldehydes and 2-oxocarboxylic esters: synthesis of chiral polysubstituted bridged bicyclic ketals

Y. Ming, X. Lv, Y. Chen and Y. Liu, Chem. Commun., 2023, 59, 8711 DOI: 10.1039/D3CC02739B

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