ORGN 635 |
A concise synthesis of structurally diverse chiral isoxazolidines and synthetic applications
| Aaron R. Minter1, Amelia A Fuller2, Bin Chen2, and Anna K. Mapp1. (1) Department of Medicinal Chemistry and Department of Chemistry, University of Michigan, 930 N University, Ann Arbor, MI 48109-1055, (2) Department of Chemistry, University of Michigan, 930 North University, Ann Arbor, MI 48109 |
| The 1,3-dipolar cycloaddition has long been regarded as a valuable strategy to access structurally diverse heterocyclic targets. A particularly useful variant of this reaction reported by Kanemasa and coworkers produces high-yielding chiral isoxazolines from a metal-dependent cycloaddition of nitrile oxides and chiral allylic alcohols. We envisioned quickly targeting a variety of complex small molecules from isoxazolidine precursors (1). A viable synthetic approach has been developed to access densely functionalized isoxazolidines and has been showcased in the synthesis of geminally disubstituted b-amino acids (2). The potential usefulness of the isoxazolidine precursors in other synthetic applications is under current investigation and has been expanded to include the development of protein•protein interaction mediating small molecules (3). 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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