Practical synthesis of (E)- and (Z)-2-silyl-3-penten-1-ols with high enantiopurity |
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Authors: | Koichiro Fukuda Keiji Tanino |
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Affiliation: | 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: | Practical methods for the synthesis of the optically active (E)- and (Z)-2-silyl-3-pentene-1-ols are described. The optically pure (E)-allylsilane was synthesized from commercially available (R)-3-butyn-2-ol in five steps involving hydrozirconation followed by alkylation of the resulting alkenylmetal with BnOCH2Cl. On the other hand, both enantiomers of the corresponding (Z)-allylsilane were prepared from commercially available dimethylphenylvinylsilane through epoxidation, the regioselective epoxide-opening reaction with 1-propynylmagnesium bromide, and the subsequent optical resolution using a lipase. |
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