Bulletin of the Chemical Society of Japan p. 4051 - 4056 (1988)
Update date:2022-08-05
Topics:
Kawashima, Masatoshi
Fujisawa, Tamotsu
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.
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