Efficient Addition of Allylsilanes to α,β-Enones Using Catalytic Indium and Trimethylsilyl Chloride

 

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Abstract

α,β-Enones undergo an efficient Hosomi-Sakurai reaction with allyltrimethylsilane, in which a catalytic amount of indium is used in the presence of trimethylsilyl chloride as an activator under mild conditions to produce the conjugate addition products in good yields.

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14a was prepared from 1,3-cyclohexadione in 5 steps (PhH, EtOH, TsOH; LDA, allyl iodide; DIBALH; H₃O⁺; Wacker oxidation).

Compound 15a was prepared from 1,3-cyclohexadione in 7 steps (PhH, EtOH, TsOH; LDA, allyl iodide; Sia₂BH, H₂O₂, NaOH; Swern oxidation; Ph₃P=CHCH₂TMS; DIBALH; H₃O⁺).