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

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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

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Publication details

The article was received on 09 Sep 2019, accepted on 02 Oct 2019 and first published on 02 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01116A
Org. Chem. Front., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9QO01116A

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