2-tert-Butyl-3-methyl-2,3-dihydroimidazol-4-one-N-oxide: A new nitrone-based chiral glycine equivalent

ORGN 104

Steven W. Baldwin, Department of Chemistry, Duke University, Box 90354, Durham, NC 27708 and Alan Long, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290.
1,3-Dipolar cycloaddition reactions using a new homochiral imidazolone-derived nitrone and a variety of alkenes provide isoxazolidines in high yield and stereoselectivity. Subsequent elaboration of the cycloadducts affords the γ-lactones of γ-hydroxy-α-amino acids as well as the optically pure amino acids themselves.

 

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