β,γ-Unsaturated α-amino ester derivatives by amination of γ-silylated α,β-unsaturated esters

The reactions of γ-silylated α,β-unsaturated esters 3a-e and 6 with NsONHCO 2Et and CaO, produce β,γ-unsaturated N-(ethoxycarbonyl) α-amino esters 4a-e and 8, isolated in 38–66 % yield, through addition of (ethoxycarbonyl)aminic function on the double bond and silyl group elimination. The reactivity...

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Bibliographic Details
Published in:Tetrahedron 1997-11, Vol.53 (46), p.15853-15858
Main Authors: Loreto, M.Antonietta, Pompei, Federica, Tardella, Paolo A., Tofani, Daniela
Format: Article
Language:English
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Summary:The reactions of γ-silylated α,β-unsaturated esters 3a-e and 6 with NsONHCO 2Et and CaO, produce β,γ-unsaturated N-(ethoxycarbonyl) α-amino esters 4a-e and 8, isolated in 38–66 % yield, through addition of (ethoxycarbonyl)aminic function on the double bond and silyl group elimination. The reactivity increases in presence of α-substituents. The reactions of γ-silylated α,β-unsaturated esters with NsONHCO 2Et and CaO, produce β,γ-unsaturated N-(ethoxycarbonyl) α-amino esters in 38–66% yields.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)10045-X