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Domino Reactions That Combine an Azido-Schmidt Ring Expansion with the Diels−Alder Reaction

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posted on 2004-12-23, 00:00 authored by Yibin Zeng, D. Srinivasa Reddy, Erin Hirt, Jeffrey Aubé
The combination of the intramolecular Schmidt reaction with the Diels−Alder reaction provides expedient access to a variety of heterocycles. Two different modes of reaction planning are presented. In one, the azide and ketone moieties necessary for the intramolecular Schmidt reaction originate on different molecules that are reacted and subsequently undergo a ring-adjustment step. Alternatively, an azido ketone can be used provided the ketone is deactivated by its presence in an enone.