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

Key words

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

• References

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