Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn,syn -3-[ N -(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates (original) (raw)

The Journal of Organic Chemistry, 1996

Abstract

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 (NEt(3)) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).

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