Abstract
Abstract The lithiation of several imidoyl chlorides 5, catalysed by substoichiometric amounts of naphthalene, followed by reaction with different electrophiles gives, after hydrolysis, the corresponding imine derivatives 6 and 9 or amines 7, depending on the reaction conditions. The imine derivatives are easily converted into the corresponding ketones by treatment either with dilute hydrochloric acid, for N-aryl derivatives, or with silica gel, for N-alkyl derivatives. The hydroxyimines obtained react with LiAlH4 to give the corresponding 1,2-aminoalcohols, as a single diastereoisomer. The same result is found when the imine moiety is in situ reduced with lithium. The 1,2-aminoalcohols obtained are easily transformed into the corresponding 1,3-oxazolidines 11 by reaction with para-formaldehyde under acidic catalysis.
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