Synthesis of α-Amino Esters via α-Nitro or α-Oxime Esters: A Review - Institut Pasteur Access content directly
Journal Articles Synthesis: Journal of Synthetic Organic Chemistry Year : 2017

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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Dates and versions

pasteur-01614363 , version 1 (10-10-2017)

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