74043-12-2Relevant academic research and scientific papers
CHEMISTRY OF THE ORGANOSILICON COMPOUNDS-165 2-TRIMETHYLSILYL-METHYL-1, 3-BUTADIENE-A VERSATILE BUILDING BLOCK FOR TERPENE SYNTHESIS
Sakurai, Hideki,Hosomi, Akira,Saito, Masaki,Sasaki, Koshi,Iguchi, Hirokazu,et al.
, p. 883 - 894 (2007/10/02)
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.
HIGHLY REGIOSELECTIVE DIELS-ALDER REACTIONS OF 2-TRIMETHYLSILYLMETHYL-1,3-BUTADIENE CATALYZED BY A LEWIS ACID AND APPLICATIONS TO SYNTHESES OF TERPENES
Hosomi, Akira,Iguchi, Hirokazu,Sasaki, Jun-ichi,Sakurai, Hideki
, p. 551 - 554 (2007/10/02)
2-Trimethylsilylmethyl-1,3-butadiene undergoes highly regioselective Diels-Alder reactions with dienophiles such as acrolein and methyl vinyl ketone catalyzed by aluminium chloride in which the "para" isomers are obtained almost exclusively.The adducts are converted readily to a variety of naturally occurring mono and sesquiterpenes.
HIGHLY REGIOSELECTIVE DIELS-ALDER REACTIONS OF 2-TRIMETHYLSILYLMETHYL- AND 2-TRIMETHYLSTANNYLMETHYL-1,3-BUTADIENE
Hosomi, Akira,Saito, Masaki,Sakurai, Hideki
, p. 355 - 358 (2007/10/02)
2-Trimethylsilylmethyl and 2-trimethylstannylmethyl-1,3-butadiene undergo facile cycloaddition with dienophiles, and show high regioselectivity with unsymmetrical dienophiles.
