Versatile method for the synthesis of 4-substituted 6-methyl-3-oxabicyclo[3.3.1]non-6-ene-1-methanol derivatives: Prins-type cyclization reaction catalyzed by hafnium triflate |
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| Authors: | Masayuki Nakamura Kenji Niiyama Takeru Yamakawa |
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| Affiliation: | Tsukuba Research Institute, Merck Research Laboratories, Banyu Pharmaceutical Company, Ltd, 3 Okubo, Tsukuba, Ibaraki 300-2611, Japan |
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| Abstract: | A versatile method for the synthesis of 4-substituted 6-methyl-3-oxabicyclo[3.3.1]non-6-ene-1-methanol derivatives has been developed using Prins-type cyclization reaction between aldehydes and O-protected/unprotected cyclohex-3-ene-1,1-dimethanol. Under optimized reaction conditions using hafnium triflate, various substrates, including functionalized benzaldehydes and heteroaromatic carbaldehydes, afforded cyclization products in high yields. |
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| Keywords: | Prins-type cyclization reaction Hafnium triflate Catalytic reaction Oxabicyclo[3.3.1]nonene |
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