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.

@article{Mukai2001Co2CO8mediatedEM,
  title={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.},
  author={C. Mukai and S. Yamaguchi and I. J. Kim and M. Hanaoka},
  journal={Chemical \& pharmaceutical bulletin},
  year={2001},
  volume={49 5},
  pages={
          613-8
        }
}
Successive treatment of 4,5-epoxy-5-methyl-7-trimethylsilyl-6-heptyne-1-ol with Co2(CO)8 at 0 degrees C and a catalytic amount of BF3 x OEt2 at -78 degrees 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. 
9 Citations
[Development of highly selective reactions based on metal carbonyls and its application to synthesis of bioactive compounds].
  • C. Mukai
  • Chemistry, Medicine
  • Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
  • 2002

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