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ChemInform Abstract: Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn, syn-3-(N-(Alkoxycarbonyl)amino) 1,2-Diols via Cyclic Sulfates.

✍ Scribed by S. J. KEMP; J. BAO; S. F. PEDERSEN


Publisher
John Wiley and Sons
Year
2010
Weight
30 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis


Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn, syn-3-(N-(Alkoxycarbonyl)amino) 1,2-Diols via Cyclic Sulfates. -The formation of the cyclic sulfates (II) from the syn,syn-amino-diols (I) provides a common intermediate for the regioselective inversion of the distal or proximal hydroxyl groups. Thermolysis form the 1,3-oxazin-2-ones (III), whereas catalytic hydrogenation under basic conditions gives the 1,3-oxazolidin-2-ones (IV). -(KEMP, S.