Studies towards the stereoselective electrophilic amination of carbanions

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A rapid development of novel and more efficient amination methods has been recorded during the past decade, mostly regarding the electrophilic amination. There are only few efficient methods for reagent-controlled stereoselective electrophilic amination compared to those based on chiral substrates or chiral catalysts. An effective stereoselective amination reagent allows greater method flexibility, due to the high availability of prochiral nucleophilic substrates. In the present work the reactivity of three types of enantiomerically pure electrophilic amination reagents (N-lithiated N-pinenyl hydroxylamines, [alpha]-chloronitroso camphor and mannofuranose derivatives, and 1-deoxy-2,3:5,6-di-O-isopropylidene-1-nitro-[alpha]-D-mannofuranose) towards carbon nucleophiles (enolates and allyl organometallic compounds) was investigated, with the aim to provide a valuable method for the stereoselective synthesis of [alpha]-amino ketones and [alpha]-amino acids.

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