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Synthesis 2017; 49(18): 4093-4110
DOI: 10.1055/s-0036-1589506
DOI: 10.1055/s-0036-1589506
review
Synthesis of α-Amino Esters via α-Nitro or α-Oxime Esters: A Review
Weitere Informationen
Publikationsverlauf
Received: 07. März 2017
Accepted after revision: 06. April 2017
Publikationsdatum:
09. August 2017 (online)
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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