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

文献情報

出版日 2019-10-02

DOI 10.1039/C9QO01116A

インパクトファクター 5.281

著者

Ying-Han Chen, Xue-Jiao Lv, Zhi-Hao You

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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