Access to α-Substituted Amino Acid Derivatives via 1,3-Dipolar Cycloaddition of α-Amino Ester Derived Nitrones
2010-02-05T00:00:00Z (GMT) by
Amino acid derived nitrones were conveniently synthesized in good-to-excellent yields by condensation of α-ketoesters with <i>N</i>-benzylhydroxylamine. The cycloaddition reactions of these nitrones with different alkenes were investigated under thermal solvent-free conditions. Considering conversions, yields, and selectivities, alkyl vinyl ethers have proven to be valuable partners to achieve this transformation, which creates a tetrafunctionalized stereogenic quaternary center. From the adducts derived from vinyl ethers, a three-step access to highly functionalized α-substituted amino acid derivatives is described.
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