Selective inversion of the proximal or distal hydroxyl groups in syn,syn-3-[N-(alkoxycarbonyl)ammo] 1,2-diols via cyclic sulfates

Article abstract of DOI:10.1021/jo961060j

The formation of cyclic sulfates (4) from syn, syn-3-[N-(benzyloxycarbonyl)amino] 1,2-diols provides a common intermediate to access other diastereomers via two inversion procedures. Thermolysis of the cyclic sulfates in acetonitrile normally leads to inversion of the distal hydroxyl group to form a 1,3-oxazin-2-one (6). Catalytic hydrogenation of the cyclic sulfates under basic conditions (NEt₃) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).