2024-03-28T12:36:32Z
https://kitami-it.repo.nii.ac.jp/oai
oai:kitami-it.repo.nii.ac.jp:00007175
2022-12-13T02:20:34Z
1:87
Construction of Terminal Conjugated Enynes: Regio- and Stereoselective Syntheses of 3-Alken-1- ynes and 1-Trimethylsilyl-3-alken-1-ynes from Alkenyldialkylboranes and (Trimethylsilyl)ethynyl Bromide
Hoshi, Masayuki
Shirakawa, Kazuya
open access
http://www.thieme-connect.de/ejournals/abstract/synthesis/doi/10.1055/s-2002-32604
Georg Thieme Verlag, M.Hoshi, K.Shirakawa, Synlett, 2002(7), 2002, 1101-1104. c 2002 Georg Thieme Verlag KG.
The cross-coupling reaction of (E)- and (Z)-1-alkenyldialkylboranes with (trimethylsilyl)ethynyl bromide proceeds in the presence of a base and a catalytic amount of Cu(acac)2 under very mild conditions to provide conjugated enynes whose carbon-carbon triple bond is in distal position. The use of 1 M NaOMe as a base exclusively affords both (E)- and (Z)-3-alken-1-ynes with high regio- and stereoselectivity, while the use of LiOH・H2O instead of 1 M NaOMe preferentially gives both (E)- and (Z)-1-trimethylsilyl-3- alken-1-ynes regio- and stereoselectively.
application/pdf
Georg Thieme Verlag
2002-07
eng
journal article
AM
https://kitami-it.repo.nii.ac.jp/records/7175
http://doi.org/10.1055/s-2002-32604
Synlett
2002
7
1101
1104
https://kitami-it.repo.nii.ac.jp/record/7175/files/4605.pdf
application/pdf
68.2 kB
2016-11-22