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

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Synthesis of α-Amino Esters via α-Nitro or α-Oxime Esters: A Review
Synthesis ( IF 2.2 ) Pub Date : 2017-08-09 , DOI: 10.1055/s-0036-1589506
Yves Janin _{1,

2} , Vincent Hervin _{1,

2} , Eloi Coutant _{1,

2} , Glwadys Gagnot _{1,

2,

3}

Affiliation

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

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

中文翻译：

通过α-硝基或α-肟酯合成α-氨基酯的研究进展

摘要

这篇综述是对已报道的通过还原α-硝基或α-肟酯中间体制备外消旋α-氨基酯的合成方法的深入调查。因此，它描述了已设计用于制备此类中间体的许多途径。这包括使用α-硝基乙酸酯，丙二酸二烷基酯，乙酰乙酸酯，草酸二乙酯以及分别使用碳氰基丙烯酸烷基酯N-氧化物或2-亚硝基丙烯酸丙烯酸烷基酯的[2 + 3]或[2 + 4]环加成物开始的合成。这篇综述还描述了使用α-硝基酯时可能发生的多种副反应。

1引言

通过缩合反应从α-硝基乙酸盐中得到2个α-氨基酯

通过α-硝基乙酸的C-烷基化或C-芳基化反应制得3个α-氨基酯

使用其他反应从α-硝基乙酸酯中提取4种α-氨基酯

5通过α-肟酯合成α-氨基酯

6通过[2 + 3]环加成合成α-氨基酯

7通过[2 + 4]环加成合成α-氨基酯

8关于α-肟酯的还原

9结论

1引言

通过缩合反应从α-硝基乙酸盐中得到2个α-氨基酯

通过α-硝基乙酸的C-烷基化或C-芳基化反应制得3个α-氨基酯