A new synthetic method for the preparation of amino sugars through an allyl cyanate-to-isocyanate rearrangement

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Abstract
A new approach for the synthesis of amino sugars using an allyl cyanate-to-isocyanate rearrangement has been developed. The key feature in this method involves introduction of the nitrogen substituent into the pyranose framework by [3,3] sigmatropic rearrangement of an allyl cyanate. Subsequent functionalization of the allylamine moiety by either hydroxylation or cyclofunctionalization completes the synthesis of two amino sugars, D-perosamine and D-vicenisamine.

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