Issue 22, 2019

Asymmetric organocatalyzed reaction sequence of 2-hydroxy cinnamaldehydes and acyclic N-sulfonyl ketimines to construct diverse chiral bridged polycyclic aminals

Abstract

Asymmetric organocatalytic annulation reactions have been developed, where both 2-hydroxy cinnamaldehydes and acyclic N-sulfonyl ketimines were used as multisite substrates (more than two reactive sites) in an iminium catalysis triggered sequential process. Notably, H2O is crucial for reactivity and selectivity, since different isolable hemiaminal intermediates were obtained in aqueous medium, thus leading to diverse chiral bridged polycyclic aminals in a highly regio- and stereoselective manner. Several other interesting transformations with the obtained aminals were also realized.

Graphical abstract: Asymmetric organocatalyzed reaction sequence of 2-hydroxy cinnamaldehydes and acyclic N-sulfonyl ketimines to construct diverse chiral bridged polycyclic aminals

Supplementary files

Article information

Article type
Research Article
Submitted
09 sep 2019
Accepted
02 okt 2019
First published
02 okt 2019

Org. Chem. Front., 2019,6, 3725-3730

Asymmetric organocatalyzed reaction sequence of 2-hydroxy cinnamaldehydes and acyclic N-sulfonyl ketimines to construct diverse chiral bridged polycyclic aminals

Y. Chen, X. Lv, Z. You and Y. Liu, Org. Chem. Front., 2019, 6, 3725 DOI: 10.1039/C9QO01116A

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