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Cobalt-Mediated [3 + 2]-Annulation Reaction of Alkenes with α,β-Unsaturated Ketones and Imines

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journal contribution
posted on 20.08.2009 by Jennifer M. Schomaker, F. Dean Toste, Robert G. Bergman
The utility of cobalt dinitrosyl complexes for the [3 + 2] annulation of alkenes with unsaturated enones and ketimines has been demonstrated. Reaction of a series of cobalt dinitrosyl/alkene adducts with conjugate acceptors in the presence of Sc(OTf)3/LHMDS formed two new C−C bonds at the carbons α to the nitrosyl groups of the substrate, leading to unusual tri- and tetracycles. Retrocycloaddition of these products in the presence of norbornadiene yielded functionalized tetrasubstituted bicyclic olefins.

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