Organic & Biomolecular Chemistry 2013-09-21

Urea-catalyzed construction of oxazinanes.

Andrea M Hardman, Sonia S So, Anita E Mattson

Index: Org. Biomol. Chem. 11(35) , 5793-7, (2013)

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Abstract

Highly functionalized oxazinanes are efficiently prepared through urea-catalyzed formal [3 + 3] cycloaddition reactions of nitrones and nitrocyclopropane carboxylates. The reaction system is general with respect to both the nitrocyclopropane carboxylates and nitrones enabling the preparation of a large family of oxazinanes, typically in high yield. This method affords access to enantioenriched oxazinane products through chirality transfer from enantioenriched nitrocyclopropane carboxylates.