Abstract
We wished to prepare planar chiral compounds by the lithiation of acetal 2-ferrocenyl-(4 S,5 S)-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.
Published Version
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