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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SYNTHESIS, Georg Thieme Verlag, 2017, 49 (18), pp.4093 - 4110. 〈10.1055/s-0036-1589506〉
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Soumis le : mardi 10 octobre 2017 - 17:50:09
Dernière modification le : jeudi 11 janvier 2018 - 06:25:29

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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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