Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn,syn-3-[N-(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (20) , 7162-7167
- https://doi.org/10.1021/jo961060j
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 (NEt3) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).Keywords
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