Sulfamate-Tethered Aza-Wacker Cyclization Strategy for the Syntheses of 2-Amino-2-deoxyhexoses: Preparation of Orthogonally Protected d-Galactosamines

Abstract

We present a new strategy for the assembly of protected d-galactosamine synthons. Our route uses a sulfamate-tethered aza-Wacker cyclization as a key step and commences from d-erythrono-1,4-lactone. This stands in contrast to most literature syntheses of 2-amino-2-deoxyhexose derivatives, as these generally employ glycals or hexoses as starting materials. This strategy may serve as a template for the assembly of many other 2-amino-2-deoxyhexoses with protection patterns difficult to access by conventional methods.