92912-11-3Relevant academic research and scientific papers
HIGHLY REGIO- AND STEREOSELECTIVE RING-OPENING REACTION OF γ-ALKENYL-γ-BUTYROLACTONES USING ALLYLSILANES-TRIMETHYLOXONIUM SALT TO AFFORD METHYL (E)-4,8-ALKADIENOATES
Fujisawa, Tamotsu,Kawashima, Masatoshi,Ando, Shogo
, p. 3213 - 3216 (1984)
γ-Alkenyl-γ-butyrolactones reacted regio- and stereoselectively with allyltrimethylsilanes in the presence of trimethyloxonium tetrafluoroborate to afford methyl (E)-4,8-alkadienoates in high yields.Synthetic utility of the present reaction was demonstrated by the synthesis of β-sinensal.
Highly Regio- and Stereoselective Ring-Opening Reaction of γ-Alkenyl-γ-butyrolactones with Allysilanes in the Presence of Trimethyloxonium Salt Leading to Methyl 4,8-Alkadienoates
Kawashima, Masatoshi,Fujisawa, Tamotsu
, p. 4051 - 4056 (2007/10/02)
The reaction of γ-alkenyl-γ-butyrolactones with allylic trimethylsilanes in the presence of trimethyl-oxonium tetrafluoroborate proceeded regio- and stereoselectively with an allylic rearrangement of the substrate to afford methyl (E)-4,8-alkadienoates in high yields.On the other hand, the ring opening of 4-hexen-6-olide afforded exclusively methyl (Z)-4,8-alkadienoates in high yields.The synthetic utility of the reaction was demonstrated by the short step synthesis of β-sinensal and β-farnesene.
