Two-Step Synthesis of α,β-Unsaturated γ-Amino Acid Esters via N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Enals and Nitroso Compounds

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-catal...

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Veröffentlicht in:Synthesis (Stuttgart) 2018-01, Vol.50 (1), p.127-133
Hauptverfasser: Liu, Qiang, Chen, Xiang-Yu, Li, Sun, Vetica, Fabrizio, Raabe, Gerhard, Enders, Dieter
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1590901