From cationic to anionic helicenes: new reactivity through umpolung.

J Org Chem

Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland.

Published: April 2011

Using a two-step reduction/metalation procedure, highly stable chiral carbenium ions are transformed into reactive carbanion intermediates. Interesting polar ketone and thioamide products are the results of this umpolung that occurs with complete retention of configuration of the helical backbone.

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http://dx.doi.org/10.1021/jo200071nDOI Listing

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