Silicon-Assisted Ring Opening of Cyclopropyl Ketones with Boron Trifluoride-Acetic Acid Complex
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
Ochiai, Masahito,Sumi, Kenzo,Fujita, Eiichi
p. 3931 - 3938
(2007/10/02)
RING OPENING OF CYCLOPROPYL KETONES ASSISTED BY THE TRIMETHYLSILYL GROUP
Cyclopropyl ketones 2 were smoothly cleaved with boron trifluoride-acetic acid under mild reaction conditions by the assistance of trimethylsilyl group to give γ,δ-enones in good yields and the reaction was applied to the formal total synthesis of cis-jasmone.
Ochiai, Masahito,Sumi, Kenzo,Fujita, Eiichi
p. 79 - 80
(2007/10/02)
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