Synthetic Communications p. 4369 - 4373 (1996)
Update date:2022-07-29
Topics:
Yang, De-Yu
Huang, Xian
Alkylselenovinyldialkylborane derivatives, obtained by hydroboration of terminal alkylselenoacetylenes 1 with dialkylboranes 2, were treated at -15°C with sodium methoxide and cuprous bromide-methyl sulfide to generate alkylselenovinylcopper intermediates which underwent stereospecific cross-coupling with allyl bromide to yield (E)-1-alkylseleno-1,4-pentadienes 3. The compounds 3 were formed with retention of configuration predetermined from the stereochemistry of the initial alkylselenovinylboranes.
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