Cyclooctanone synthesis via a formal [6+2] cycloaddition reaction of a dicobalt acetylene complex |
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Authors: | Katsuhiko Mitachi Masaaki Miyashita |
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Institution: | a Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan b Department of Applied Chemistry, Faculty of Engineering, Kogakuin University, Hachioji 192-0015, Japan |
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Abstract: | An efficient formal 6+2] cycloaddition reaction of a new six-carbon unit with enol silyl ether was developed on the basis of a dicobalt hexacarbonyl propargyl cation species. Under the influence of EtAlCl2, 6-benzoyloxy-2-(triisopropylsilyloxy)-1-hexen-4-yne-dicobalthexacarbonyl reacted with enol triisopropylsilyl ethers to yield 7-(triisopropylsilyloxy)-3-cyclooctyn-1-one-dicobalthexacarbonyl derivatives in good yield. The reactions with cyclic enol silyl ethers as well as acyclic enol silyl ethers exhibited remarkably high diastereoselectivity. |
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