Asymmetric organocatalyzed reaction sequence of 2-hydroxy cinnamaldehydes and acyclic N-sulfonyl ketimines to construct diverse chiral bridged polycyclic aminals
Literature Information
Publication Date
2019-10-02
DOI
10.1039/C9QO01116A
Impact Factor
5.281
Authors
Ying-Han Chen, Xue-Jiao Lv, Zhi-Hao You
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
Methyl 2-amino-4-(4-chlorophenyl)-5-pyrimidinecarboxylate
CAS Number:
1133115-56-6
Molecular Formula:
C12H10ClN3O2
![(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid structure](https://static.chemtradehub.com/structs/865/865689-24-3-5fef.webp "(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid structure")
(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid
CAS Number:
865689-24-3
Molecular Formula:
C12H19NO4
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