57217-07-9Relevant academic research and scientific papers
Carboindation of Alkynes. Regio- and Stereoselective Allylation of Carbon-Carbon Triple Bonds of Alkynols by Allylic Indium Reagents
Araki, Shuki,Imai, Akira,Shimizu, Ken,Yamada, Masafumi,Mori, Akihiro,Butsugan, Yasuo
, p. 1841 - 1847 (1995)
Allylindium sesquihalides undergo smooth allylindation with terminal alkynes bearing a neighboring hydroxyl group at 100-140 deg C to give allylalkenols.The coupling occurred regioselectively at the γ-carbon of the allylindium reagents via syn-addition, whereas the regioselectivity concerning the alkynol depends upon the structures of both allylindium and alkynol.The allylation of nonfunctionalized alkynes is less efficient, requiring higher reaction temperature (150-180 deg C) and giving lower yields.Mechanistic considerations suggest a hydroxyl-assisted concerted process for the allylindation of alkynols, whereas a radical pathway is more likely for nonfunctionalized alkynes.Three monoterpene alcohols, i.e., yomogi alcohol, achillenol, and isomyrcenol, were conveniently prepared via allylindation of appropriate alkynols.
Carboindation of alkynols. A facile synthesis of yomogi alcohol
Araki, Shuki,Imai, Akira,Shimizu, Ken,Butsugan, Yasuo
, p. 2581 - 2582 (2007/10/02)
Carboindation of alkynols by ally lie indium sesquihalides proceeded in DMF at 100 - 140 °C via a synaddition; yomogi alcohol was prepared in onepot by this method.
