6994-89-4Relevant articles and documents
Preparation of ketones from esters via substituted cyclopropanols. Application to the synthesis of (±)-ipsenol, (±)-ipsdienol and amitinol, the components of aggregation pheromones of the Ips bark beetles
Chevtchouk, Timour A.,Isakov, Vladimir E.,Kulinkovich, Oleg G.
, p. 13205 - 13210 (1999)
The regioselective two-step sequence of bromination- dehydrobromination of 2-(2,2-diethoxy)-1-methyl-1-cyclopropanol affords 3-(2,2-diethoxyethyl)-3-buten-2-one in high yield. The reduction of the latter, followed by chlorination and dehydrochlorinatiou, provides 2-(2,2-diethoxyethyl)-1,3-butadiene that was used as a building block for the synthesis of (±)- ipsenol, (±)ipsdienol and amitinol - the components of aggregation pheromones of the Ips bark beetles.
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 (2007/10/02)
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.
PALLADIUM CATALYZED COUPLING OF ORGANOSTANNANES WITH VINYL EPOXIDES
Tueting, David R.,Echavarren, Antonio M.,Stille, J. K.
, p. 979 - 992 (2007/10/02)
The coupling reaction of organotin reagents with vinyl epoxides, catalyzed by palladium, takes place at ambient temperatures, regioselectively, giving predominately the 1,4-addition product.Both aryl- and vinylstannanes undergo coupling in high yields, wh
