Journal article

Authors list: Beeck, S; Ahles, S; Wegner, HA

Publication year: 2021

Pages: e202104085-

Journal: Chemistry - A European Journal

Volume number: 28

Issue number: 5

ISSN: 0947-6539

eISSN: 1521-3765

Open access status: Green

DOI Link: https://doi.org/10.1002/chem.202104085

Publisher: Wiley

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.

Harvard Citation style: Beeck, S., Ahles, S. and Wegner, H. (2021) Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels-Alder/Substitution Reaction, Chemistry - A European Journal, 28(5), p. e202104085. https://doi.org/10.1002/chem.202104085

APA Citation style: Beeck, S., Ahles, S., & Wegner, H. (2021). Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels-Alder/Substitution Reaction. Chemistry - A European Journal. 28(5), e202104085. https://doi.org/10.1002/chem.202104085