Abstract
The reaction of ferrocenylalkenes with chloromethyl alkyl ethers catalyzed by Lewis acids gives 3-alkoxy-1-ferrocenyl carbocations, which can be trapped by nucleophiles to give 1,3-disubstituted ferrocenylalkane derivatives. The application of this reaction to the preparation of chiral 3-hydroxy-1-ferrocenylalkylamines is described; their structures and conformations have been elucidated by NMR spectroscopy. The stereochemical course of the alkoxymethylation reaction involves “ exo” attack of the chloromethyl ether at the β carbon of the double bond relative to the ferrocene, and subsequent “ exo” attack of the nucleophile at the carbocationic centre formed in the first step.
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