Unexpected reactions of ferrocene acetal derived from tartaric acid with alkyllithium: competition between proton abstraction and nucleophilic attack |
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Authors: | Wanbin Zhang Fang Xie Toshiyuki Kida Isao Ikeda |
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Affiliation: | a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China b Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan |
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Abstract: | We wished to prepare planar chiral compounds by the lithiation of acetal 2-ferrocenyl-(4S,5S)-bis(methoxymethyl)-1,3-dioxolane (1) with butyllithium followed by the reaction with an electrophile. However, the desired products were not observed and two unexpected products, 1-ferrocenyl-1-pentanol (4) of the nucleophilic attack product and 2-ferrocenyl-4,5-dimethylene-1,3-dioxolane (5) of the proton abstraction product, were isolated. Because the nucleophilic attack on acetal carbon is rarely reported so far and both products 4 and 5 may have some potential uses in organic synthesis, these unexpected reactions are investigated in detail. The mechanisms of these reactions are discussed. |
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Keywords: | Lithiation ortho-Directing groups Ferrocene Butyllithium Dimethyl smallcaps" >l-tartrate Ferrocene acetal Ferrocene alcohol |
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