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

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
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https://hal-pasteur.archives-ouvertes.fr/pasteur-01614363
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Submitted on : Tuesday, October 10, 2017 - 5:50:09 PM
Last modification on : Thursday, April 11, 2019 - 4:02:50 PM

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Vincent Hervin, Eloi P. Coutant, Glwadys Gagnot, Yves Janin. Synthesis of α-Amino Esters via α-Nitro or α-Oxime Esters: A Review. SYNTHESIS, Georg Thieme Verlag, 2017, 49 (18), pp.4093 - 4110. ⟨10.1055/s-0036-1589506⟩. ⟨pasteur-01614363⟩

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