Related Experiment Video
Updated: Aug 15, 2025
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
One-Step Asymmetric Construction of 1,4-Stereocenters via Tandem Mannich-Isomerization Reactions Mediated by a
Yu Deng1,2, Xiaohuo Shi3, Guangfa Shi1
1Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province China.
Abstract:
The construction of chiral motifs containing nonadjacent stereocenters stands out as a major challenge as they are usually constructed in separate steps utilizing different chiral catalysts. Therefore, the development of new strategies to streamline the construction of such complex motifs has become a major focus of asymmetric synthesis. We report here an unprecedented asymmetric tandem Mannich-isomerization reaction that allows the direct construction of 1,4-stereocenters in a highly stereoselective manner. This asymmetric transformation demonstrated the potential of a tandem nucleophilic addition-isomerization reaction as a broadly useful strategy for the efficient construction of 1,4-stereocenters. Notably, this tandem reaction was mediated by a single chiral betaine as a dual-functional catalyst, promoting first an enantioselective intermolecular C-C bond forming reaction and next a stereoselective intramolecular 1,3-proton transfer reaction.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
01:28Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
01:29Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
02:05Prochirality