Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 49, Pages 14845-14848Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502872
Keywords
annulation; copper; heterocycles; small-ring compounds; synthetic methods
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A practical copper-catalyzed direct oxidative cyclopropanation of electron-deficient alkenes with acetophenone derivatives is reported. The dehydrogenative annulation involves a double C-H bond functionalization at the alpha-position of the ketone using di-tert-butyl peroxide as oxidant. The broad scope of the reaction and excellent functional-group tolerance is demonstrated for the stereoselective synthesis of fused cyclopropanes. The developed transformation revealed an unprecedented reactivity for copper-catalyzed processes.
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