Recent studies have produced a number of methods for oxime cyclizations onto β,γ-alkenes under electrophilic or radical conditions. We present the utility of a Co(II)-mediated radical reaction in the context of carbohydrates to explore factors that control the stereoselectivity of oxygen introduction onto pendant alkenes. Protected C-linked galacto-alkenes are transformed to the C-2 oxime for cyclization studies. The resultant isooxazolines are further reduced to yield N-acetylgalactosamines with a free hydroxyl on the carbon-linkage.

C-Galactosyl oxime cycylizations onto pendant alkenes

2019 Spring National Meeting

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