Cation−n Control of Regiochemistry of Intramolecular Schmidt Reactions en Route to Bridged Bicyclic Lactams
Organic Letters2009Vol. 11(19), pp. 4386–4389
Citations Over TimeTop 14% of 2009 papers
Abstract
The regiochemistry of the intramolecular Schmidt reaction of 2-azidoalkylketones is controlled by placing a thioether substituent at the position adjacent to the ketone to provide access to a family of unsubstituted medium bridged twisted amides. This outcome is ascribed to the presence of stabilizing through-space interactions between the diazonium cation and the n electrons on heteroatom and does not require a locked conformation of the ketone.
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