89664-40-4Relevant academic research and scientific papers
Silicon-Assisted Ring Opening of Cyclopropyl Ketones with Boron Trifluoride-Acetic Acid Complex
Ochiai, Masahito,Sumi, Kenzo,Fujita, Eiichi
, p. 3931 - 3938 (2007/10/02)
2-(Trimethylsilylmethyl)cyclopropyl ketones were smoothly cleaved with boron trifluoride-acetic acid complex under mild reaction conditions with the assistance of the trimethylsilyl group to give γ,δ-enones in good yields.The major effect of the trimethylsilyl group in the ring opening of the cyclopropyl ketones was unambiguously confirmed in the dicyclopropyl ketone 15: one of its two cyclopropyl rings, which has a trimethylsilylmethyl group, was selectively cleaved.Furthermore, the reaction was applied to the formal total synthesis of cis-jasmone.Keywords - ring opening of cyclopropyl ketone; trimethylsilyl group; γ,δ-enone; cis-jasmone; allylsilane; boron trifluoride-acetic acid
