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| - Directing Abilities of Alcohol-Derived Functional Groups in theHydroformylation of Olefins
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| - The hydroformylation of allylic and homoallylic alcohols and their derivatives using cationic andneutral rhodium complexes has been examined. The highest diastereoselectivity (87:13) was observedin the reaction of 1-methoxymethoxy-2-methylenecyclohexane. Higher yields and similar selectivitieswere obtained in the reaction of the TBDMS-protected alcohol. The major diastereomer resultsfrom hydroformylation syn to the functional group, which would suggest a directing effect. However,hydroformylation of 3-methylene-1-cyclohexanol derivatives occurs on the face opposite to thedirecting group in the major isomer. These data, in addition to the results of hydroformylation of1-methyl-2-methylenecyclohexane, suggest that inherent conformational preferences are of significant importance in determining the product distribution and that the directing power of simplealcohols and their derivatives is moderate at best under the conditions examined in this study.
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