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
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概要
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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.
- Georg Thieme Verlagの論文
Georg Thieme Verlag | 論文
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