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Dienamine-Induced Divinylcyclopropane-Cycloheptadiene Rearrangements

preprint
submitted on 05.12.2018, 19:32 and posted on 06.12.2018, 14:07 by Caroline Apel, Sven Sören Hartmann, Dieter Lentz, Mathias Christmann
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 in situgenerated divinylcyclopropanes. The reactive motif is generated by condensation of 4-(2-vinylcyclopropyl)but-2-enal derivatives and a secondary amine catalyst to form a transient dienamine. The cycloheptadiene products can be obtained in high yield and excellent diastereoselectivity. Importantly, the reaction was demonstrated to be stereospecific, proceeds under mild conditions, and shows broad functional group tolerance.

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in Angewandte Chemie International Edition

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Email Address of Submitting Author

mathias.christmann@fu-berlin.de

Institution

Freie Universität Berlin

Country

Germany

ORCID For Submitting Author

0000-0001-9313-2392

Declaration of Conflict of Interest

No conflict of interest

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Read the published paper

in Angewandte Chemie International Edition

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