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oai:kitami-it.repo.nii.ac.jp:00007175 2026-02-16T06:20:09Z 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