Co2(CO)8-mediated Endo Mode Cyclization of Epoxy-alcohol: Synthesis of 2-Ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-Ethynyl-3-hydroxy-3-methyltetrahydropyran Derivatives.

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  • ChemInform Abstract: Co<sub>2</sub>(CO)<sub>8</sub>‐Mediated endo Mode Cyclization of Epoxy‐Alcohol: Synthesis of 2‐Ethynyl‐3‐hydroxy‐2‐methyltetrahydropyran and 2‐Ethynyl‐3‐hydroxy‐3‐methyltetrahydropyran Derivatives.

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Successive treatment of 4, 5-epoxy-5-methyl-7-trimethylsilyl-6-heptyne-1-ol with Co2(CO)8 at 0 °C and a catalytic amount of BF3·OEt2 at −78 °C gave the tetrahydropyran derivatives with the cobalt-complexed moiety. Similarly 4, 5-epoxy-4-methyl-7-trimethylsilyl-6-heptyne-1-ol underwent ring closure under the above conditions to provide the corresponding tetrahydropyran derivatives. The preferential endo mode cyclization over the exo one was observed in these experiments.

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