Urea-catalyzed construction of oxazinanes.

Organic & biomolecular chemistry (2013-08-03)
Andrea M Hardman, Sonia S So, Anita E Mattson
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Mattson Difluoroborate Urea
Sigma-Aldrich
Potassium 3-ethoxycarbonylbenzoyltrifluoroborate
Sigma-Aldrich
Mattson Boronate Urea Pinacol Ester

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