Synthesis of chiral 1,3-oxazin-2-ones from carbohydrate derivatives

ORGN 80

Jean Rene Ella-Menye, Vibha Sharma, and Guijun Wang. Department of Chemistry, University of New Orleans, 2000 Lakeshore drive, New Orleans, LA 70148
Chiral 5-hydroxymethyl 2-oxazolidinones (I) are important core structures in many pharmaceutical compounds and intermediates in the synthesis of chiral aminoalcohols. The homologous cyclic carbamate tetrahydro oxazinones are also useful intermediates in synthesizing natural products and 1,3-aminoalcohols. The oxazinanone derivatives are biologically important compounds which are being explored as drugs for inflammatory disease, ulcer, allergy, asthma and arthritis. The chiral version of the homologous 6-substituted 1,3-oxazinan-2-ones are difficult to synthesize. Very few methods of synthesizing chiral 1,3-oxazinanones are available in the literature, this include one asymmetric synthesis of the chiral oxazinanones from aspartic acid. In this paper, we report a new synthetic route to chiral 6-hydroxymethyl tetrahydro 1,3-oxazin-2-ones (II) and their analogues from carbohydrate derivatives.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004