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Synthesis of α-Amino Esters via α-Nitro or α-Oxime Esters: A Review

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This review is an in-depth survey of the reported synthetic approaches for the preparation of racemic α-amino esters via the reduction of α-nitro or α-oxime ester intermediates. Accordingly, it describes… Click to show full abstract

This review is an in-depth survey of the reported synthetic approaches for the preparation of racemic α-amino esters via the reduction of α-nitro or α-oxime ester intermediates. Accordingly, it describes the many pathways that have been designed to prepare such intermediates­. This includes synthesis starting with α-nitroacetates, dialkyl malonates, acetoacetates, diethyl oxalates as well as [2+3] or [2+4] cycloadditions using, respectively, alkyl carbonocyanidate N -oxides or alkyl 2-nitrosoacrylates. This review also contains the description of a myriad of side reactions which can occur when working with α-nitro esters­. 1 Introduction 2 α-Amino Esters from α-Nitroacetates via Condensation Reactions 3 α-Amino Esters via C -Alkylation or C -Arylation of α-Nitroacetates 4 α-Amino Esters from α-Nitroacetates Using Other Reactions 5 Synthesis of α-Amino Esters via α-Oxime Esters 6 Synthesis of α-Amino Esters via [2+3] Cycloadditions 7 Synthesis of α-Amino Esters via [2+4] Cycloadditions 8 On the Reduction of α-Oxime Esters 9 Conclusion

Keywords: oxime esters; amino esters; esters via; synthesis amino

Journal Title: Synthesis
Year Published: 2017

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