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

Scott J. Kemp; Jianming Bao; Steven F. Pedersen

doi:10.1021/jo961060j

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

J Org Chem. 1996 Oct 4;61(20):7162-7167. doi: 10.1021/jo961060j.

Authors

Scott J. Kemp¹, Jianming Bao, Steven F. Pedersen

Affiliation

¹ Department of Chemistry, University of California, Berkeley, California 94720.

PMID: 11667620
DOI: 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 (NEt(3)) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).