Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 15, Pages 5075-5079Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813880
Keywords
Cope rearrangement; cycloheptadienes; cyclopropanes; organocatalysis; pericyclic reactions
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Funding
- Fonds der Chemischen Industrie
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Sigmatropic rearrangements constitute an important group of pericyclic reactions. In contrast to cycloaddition reactions, examples of catalytic variants of electrocyclic reactions and sigmatropic rearrangements are still scarce in the chemical literature. Herein, we report the first organocatalytic Cope rearrangement of insitu-generated divinylcyclopropanes. The reactive motif was generated by condensation of 4-(2-vinylcyclopropyl)but-2-enal derivatives with a secondary amine catalyst to form a transient dienamine. The cycloheptadiene products could be obtained in high yield and excellent diastereoselectivity. Importantly, the reaction was demonstrated to be stereospecific, proceeding under mild conditions, while exhibiting broad functional group tolerance.
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