Chemistry of Organosilicon Compounds. 171. Isoprenylation of Carbonyl Compounds with 2--1,3-butadiene Initiated by a Catalytic Amount of Tetra-n-butylammonium Fluoride. The Most Convenient Route to Ipsenol and Ipsdienol
CHEMISTRY OF THE ORGANOSILICON COMPOUNDS-165 2-TRIMETHYLSILYL-METHYL-1, 3-BUTADIENE-A VERSATILE BUILDING BLOCK FOR TERPENE SYNTHESIS
Two types of synthetically useful reactions of 2-trimethylsilylmethyl-1,3-butadiene (7) are discussed.Reactions of 7 with acid chlorides, aldehydes, ketones and acetals activated by a Lewis acid give isoprenylated compounds, while 7 undergoes the Diels-Alder reaction whit dienophiles.High regiospecificity of the reaction qualifies 7 for a versatile building block of terpene synthesis.