First enantioselective synthesis of a 1-(trimethylsilyl)alkylamine

Abstract Reduction of n -propanoyltrimethylsilane NH-imine with the complex hydride LiBH 4 /diethyltartrate in THF yielding enantiomerically enriched 1-(trimethylsilyl)butylamine with a 60% enantiomeric excess is the first example of the enantioselective synthesis of such an amine. Other combinations of solvent (ether or THF), hydride (NaBH 4 or LiAlH 4 ) and chiral inductor (mono- or diol) failed.