Selective Synthesis of Chiral Dioxabicyclo[4.4.0]decane and Dioxabicyclo[5.3.0]decane from 3,4-Bisallyloxy-but-1-yne Derivatives via Ruthenium-Catalyzed En-yn-ene Metathesis

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Abstract

We prepared a series of chiral 3,4-bisallyloxy-but-1-ynes having syn and anti configurations. Treatment of these substrates with Grubbs catalyst Cl2(PCy3)2Ru=CHPh (3 mol %) preferably gave chiral dioxabicyclo[4.4.0]decane (yields > 55%) in addition to dioxabicyclo[5.3.0]decane in minor proportions. On substitution of the 4-allyloxy group of these substrates with a 4-but-2-enyloxy group, the metathesis reactions produced only dioxabicyclo[5.3.0]decane in the presence of Grubbs ruthenium-imidazolidene carbene catalyst.

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