Guijun Wang, R. Hollingsworth
Nov 17, 2000
Citations
1
Influential Citations
16
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract A simple high-yield three-step route to O -tritylated optically active 5-hydroxymethyl oxazolidinones from optically active 3-hydroxy-γ-butyrolactones is described. The key intermediate is the 4- O -trityl ether of homochiral 3,4-dihydroxybutyramide, which is obtained in quantitative yield from 3-hydroxy-γ-butyrolactone by treatment with ammonia. It is readily transformed to the oxazolidinone by Hoffmann rearrangement in a two-phase system. The carbonyl group in the oxazolidinone is derived from C-1 of the amide, and a separate carbonylation reaction is not required. Oxazolidinones are key compounds in drug synthesis especially in the areas of antibacterials and behavior disorder therapy.