title: Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn,syn-3-[N-(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates.
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).
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720.
authors.forename: Scott J.
authors.initials: SJ
authors.lastname: Kemp
authors.forename: Jianming
authors.initials: J
authors.lastname: Bao
authors.forename: Steven F.
authors.initials: SF
authors.lastname: Pedersen