a,a-Disubstituted selenoamides are synthesized from terminal acetylenes, selenium, amines and allylic bromides in good to high yields; their reduction with L i A l b affords alkenylamines quantitatively.

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The deprotonation of α-monosubstituted selenoamides with LDA followed by allylation gives γ,δ-unsaturated selenoamides in good to high yields. In the initial step, allylation may take place at the selenium atom of lithium eneselenolates to form allylic vinyl selenides, which then undergo seleno-Claisen rearrangement. As allylic bromides, γ,γ-disubstituted compounds such as geranyl and neryl bromides could also be used to give products that incorporated tertiary-quaternary stereogenicity with high efficiency.

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