The reaction of propiolate acetylides with nitrones. Synthesis of γ-amino-α,β-ethylenic acid derivatives

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Abstract

Nitrones react with the lithium anions of ethyl and t-butyl propiolates to give acetylenic N-hydroxylamines. The reduction of these compounds with Zn in the presence of an acid leads to E and Z α,β-ethylenic-γ-aminoacids derivatives. The stereoselectivity of these reactions was studied.

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Denis, J. N., Tchertchian, S., Tomassini, A., & Vallée, Y. (1997). The reaction of propiolate acetylides with nitrones. Synthesis of γ-amino-α,β-ethylenic acid derivatives. Tetrahedron Letters, 38(31), 5503–5506. https://doi.org/10.1016/S0040-4039(97)01210-0

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