Synthesis 2017; 49(18): 4093-4110
DOI: 10.1055/s-0036-1589506
review
© Georg Thieme Verlag Stuttgart · New York

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

Vincent O. Hervina, b, Eloi P. Coutanta, b, Glwadys Gagnota, b, c, Yves L. Janin*a, b
  • aUnité de Chimie et Biocatalyse, Département de Biologie Structurale et Chimie, Institut Pasteur, 28 rue du Dr Roux, 75724 Paris Cedex 15, France   Email: yves.janin@pasteur.fr
  • bUnité Mixte de Recherche 3523, Centre National de la Recherche Scientifique, 28 rue du Dr Roux, 75724 Paris Cedex 15, France
  • cUniversité Paris Descartes, Sorbonne Paris Cité, 12 rue de l’École de Médecine, 75006 Paris, France
Further Information

Publication History

Received: 07 March 2017

Accepted after revision: 06 April 2017

Publication Date:
09 August 2017 (eFirst)

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