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Copper‐Catalyzed (2+1) Annulation of Acetophenones with Maleimides: Direct Synthesis of Cyclopropanes
Author(s) -
Manna Srimanta,
Antonchick Andrey P.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201502872
Subject(s) - annulation , cyclopropanation , chemistry , acetophenone , catalysis , reactivity (psychology) , ketone , copper , double bond , medicinal chemistry , peroxide , combinatorial chemistry , functional group , stereoselectivity , organic chemistry , medicine , polymer , alternative medicine , pathology
A practical copper‐catalyzed direct oxidative cyclopropanation of electron‐deficient alkenes with acetophenone derivatives is reported. The dehydrogenative annulation involves a double CH bond functionalization at the α‐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.