ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels-Alder/Substitution Reaction.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Lewis Acid-Catalyzed Domino Inverse Electron-Demand Diels-Alder/Thermal Ring Expansion Reaction for the Synthesis of Arene-Annulated Eight-Membered Nitrogen Heterocycles.Organic letters · 2025Article
- Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels-Alder/Substitution Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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3 authors.
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Abstract
An enantioselective domino process for the synthesis of substituted 1,2-dihydronaphthalenes has been developed by the combination of chiral amines and a bidentate Lewis acid in an orthogonal catalysis. This new method is based on an inverse electron-demand Diels-Alder and a subsequent group exchange reaction. An enamine is generated in situ from an aldehyde and a chiral secondary amine catalyst that reacts with phthalazine, activated by the coordination to a bidentate Lewis acid catalyst. The absolute configuration of the product is controlled by chiral information provided by the amine. The formed ortho-quinodimethane intermediate is then transformed via a group exchange reaction with thiols. The new method shows a broad scope and tolerates a wide range of functional groups with enantiomeric ratios up to 91 : 9. All-in-all, this enantioselective synthesis tool provides an easy access to complex 1,2-dihydronaphthalenes starting from readily available phthalazine, aldehydes and thiols in a combinatorial way.
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