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

Vincent Hervin (1) , Eloi P. Coutant (1) , Glwadys Gagnot (1, 2) , Yves L Janin (1)

1 Chimie et Biocatalyse
2 UPD5 - Université Paris Descartes - Paris 5

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: α-nitro esters; α-oxime esters; α-amino esters; cycloadditions [2+3]; cycloadditions [2+4]; nitrosoacrylate; nitrile oxide

Domains: Organic chemistry

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⟩