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The formation of asymmetric carbon-carbon and carbon-heteroatom bonds by lithiation-substitution at a carbon adjacent to nitrogen can be accomplished by deprotonations or destannylations, followed by reaction with electrophiles. Applications of these sequences for amine elaboration are summarized for reactions controlled by chiral ligands and chiral auxiliaries. Notable features include syntheses...
Oxidation of the β-substituted highly enantioenriched aldehydes obtained by hydrolysis of the 3,3-disubstituted enecarbamates affords enantioenriched β-substituted acids and esters. Lithiation of enantioenriched 3,3-disubstituted enecarbamates and subsequent reaction with electrophiles provides vinylically substituted enecarbamates. The use of benzyl and alkyl halide electrophiles affords α-substituted...
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