Regio- and stereoselective synthesis of (E)-1-alkylseleno-1,4-pentadienes by cross-coupling of allyl bromide with alkylselenovinylcoppers from alkylselenovinyldialkylboranes

Article abstract of DOI:10.1080/00397919608003839

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.

Full text of DOI:10.1080/00397919608003839

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Synthetic Communications: An
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Communication of Synthetic
Organic Chemistry
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Regio-and Stereoselective
Synthesis of (E)-1-
Alkylseleno-1, 4-Pentadienes
by Cross-Coupling of
Allyl Bromide with Alkyl-
selenovinylcoppers from
Alkylselenovinyldialkylboranes
De-Yu Yang a & Xian Huang a
a Department of Chemistry , Hangzhou University ,
Hangzhou, 310028, China
Published online: 23 Aug 2006.
To cite this article: De-Yu Yang & Xian Huang (1996) Regio-and Stereoselective
Synthesis of (E)-1-Alkylseleno-1, 4-Pentadienes by Cross-Coupling of Allyl Bromide
with Alkyl-selenovinylcoppers from Alkylselenovinyldialkylboranes, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 26:23, 4369-4373, DOI: 10.1080/00397919608003839
To link to this article: http://dx.doi.org/10.1080/00397919608003839
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