シンコニン由来の４級アンモニウムフルオリドを利用した触媒反応：Morita-Baylis-Hillman タイプ付加体の合成

抄録

We have developed the unprecedented reaction of 1-phenyl-2-(trimethylsilyl)acetylene with aromatic aldehydes to produce the highly Z-selective β-branched Morita-Baylis-Hillman-type adducts catalyzed by the quaternary ammonium fluoride derived from cinchonine, and revealed the unusual reactivity of this ammonium fluoride compared with TBAF. In the course of study about the mechanism, it was found that (1,3-diaryl-2-propynyl) trimethylsilyl ethers, which is postulated as intermediates in this reaction, were easy to isomerize to corresponding silyl allenolates by catalytic KOt-Bu under very mild conditions. The allenolates in situ react with various aldehydes to afford Z-selective β-branched Morita-Baylis-Hillman-type adducts in one-pot reaction.

fig.1