ORGN 290 |
Synthesis of highly substituted beta-amino acids via chiral isoxazolines
| Amelia A. Fuller1, Bin Chen1, Aaron R. Minter2, and Anna K. Mapp2. (1) Department of Chemistry, University of Michigan, 930 N. University, Ann Arbor, MI 48109, (2) Department of Medicinal Chemistry and Department of Chemistry, University of Michigan, 930 N University, Ann Arbor, MI 48109-1055 |
| β-Amino acids are an important class of compound as they have found application as precursors to β-lactams, are present in natural products, and have been incorporated into oligomers (β-peptides) for peptidomimetic studies. While β-peptides incorporating highly substituted β-amino acid constituents are predicted to have interesting structural properties, they remain largely unexplored, likely due to the challenges of synthesizing these sterically encumbered β-amino acids. The method we have developed uses chiral isoxazolines as key intermediates to accommodate the synthesis of this challenging subclass of β-amino acids. Diverse substrates can be accessed by this method by varying the isoxazoline substituents and by appropriate choice of nucleophile for addition to the isoxazoline. Recent efforts have been directed at accessing complex, novel β-amino acid structures as shown in the scheme that will serve to expand the substrates available for further study and application. 
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