Access to alpha-Substituted Amino Acid Derivatives via 1,3-Dipolar Cycloaddition of alpha-Amino Ester Derived Nitrones

作者:Nguyen Thanh Binh; Beauseigneur Alice; Martel Arnaud; Dhal Robert; Laurent Mathieu; Dujardin Gilles*
来源:Journal of Organic Chemistry, 2010, 75(3): 611-620.
DOI:10.1021/jo902107j

摘要

Amino acid derived nitrones were conveniently synthesized in good-to-excellent yields by condensation of alpha-ketoesters with N-benzylhydioxylamine. 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 alpha-substituted amino acid derivatives is described.

  • 出版日期2010-2-5