Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 22, Pages 8491-8496Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202000838
Keywords
cycloaddition; Diels-Alder reaction; hydrogen bonding; organocatalysis; synthetic methods
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Funding
- ICSN
- CNRS
- Saclay University
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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.
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