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Synthesis 2018; 50(01): 127-133
DOI: 10.1055/s-0036-1590901
DOI: 10.1055/s-0036-1590901
paper
Two-Step Synthesis of α,β-Unsaturated γ-Amino Acid Esters via N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Enals and Nitroso Compounds
Further Information
Publication History
Received: 02 August 2017
Accepted: 11 August 2017
Publication Date:
07 September 2017 (online)
Abstract
An efficient strategy for the synthesis of various of α,β-unsaturated γ-amino acid esters has been established employing N-heterocyclic carbene catalyzed [4+2] cycloadditions of β-methyl enals and aromatic nitroso compounds to afford 1,2-oxazin-6-ones in good yields. A subsequent acid-catalyzed esterification under ring opening yields the γ-amino enoates in good yields.
Key words
γ-amino enoate - asymmetric synthesis - organocatalysis - N-heterocyclic carbenes - nitroso compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590901.
- Supporting Information
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