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Enantioselective Redox‐Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels–Alder Reactions
Author(s) -
Varlet Thomas,
Gelis Coralie,
Retailleau Pascal,
Bernadat Guillaume,
Neuville Luc,
Masson Géraldine
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202000838
Subject(s) - enantioselective synthesis , quinone , redox , chemistry , diels–alder reaction , phosphoric acid , catalysis , selectivity , organocatalysis , diene , combinatorial chemistry , organic chemistry , natural rubber
An efficient enantioselective construction of tetrahydronaphthalene‐1,4‐diones as well as dihydronaphthalene‐1,4‐diols by a chiral phosphoric acid catalyzed quinone Diels–Alder reaction with dienecarbamates is reported. The nature of the protecting group on the diene is key to the success of achieving high enantioselectivity. The divergent “redox” selectivity is controlled by using an adequate amount of quinones. Reversible redox switching without erosion of enantioselectivity was possible from individual redox isomers.