TY - DATA T1 - Access to α-Substituted Amino Acid Derivatives via 1,3-Dipolar Cycloaddition of α-Amino Ester Derived Nitrones PY - 2010/02/05 AU - Thanh Binh Nguyen AU - Alice Beauseigneur AU - Arnaud Martel AU - Robert Dhal AU - Mathieu Laurent AU - Gilles Dujardin UR - https://acs.figshare.com/articles/journal_contribution/Access_to_Substituted_Amino_Acid_Derivatives_via_1_3_Dipolar_Cycloaddition_of_Amino_Ester_Derived_Nitrones/2793790 DO - 10.1021/jo902107j.s001 L4 - https://ndownloader.figshare.com/files/4488157 KW - adduct KW - NitronesAmino KW - ketoester KW - Access KW - Dipolar KW - Ester KW - Derivative KW - conversion KW - tetrafunctionalized stereogenic quaternary center KW - Derived KW - access KW - selectivitie KW - Substituted KW - transformation KW - alkene KW - alkyl vinyl ethers KW - cycloaddition reactions KW - condensation KW - nitrone KW - vinyl ethers KW - yield KW - acid derivatives KW - Cycloaddition KW - Amino N2 - Amino acid derived nitrones were conveniently synthesized in good-to-excellent yields by condensation of α-ketoesters with N-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. ER -