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Interrupting the Nazarov Cyclization with Bromine

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posted on 18.11.2016, 00:00 by Devon J. Schatz, Yonghoon Kwon, Thomas W. Scully, F. G. West
The generation of dibrominated cyclopentenones via an interrupted Nazarov cyclization is reported. The installation of two bromine atoms occurs at the α and α′ positions of the cyclopentenyl scaffold via successive nucleophilic and electrophilic bromination of the 2-oxidocyclopentenyl cation and its resulting enolate. Notably, the reaction proceeds with good diastereoselectivity, favoring the symmetrical product.