Ligands binaphthylamine

Ytterbium and lutetium ionic complexes, derived from enantiopure substituted (R)-binaphthylamine ligands of the general formula [Li(THF) ][Ln[(f )C2oHi2(NR)2]2], have been investigated as catalysts for hydroamination/cyclization of several unsatu- rated amines CH2=CH(CH2) C(R2)CH2NH2 (n = 1 or 2). Complexes with isopropyl or cyclohexyl substituents on nitrogen atoms were found to be efficient catalysts for the formation of N-containing heterocycles under mild conditions with enantiomeric excesses up to 78%.124... 

Scheme 10.80 Y-catalysed hydroaminations of aminoalkenes with binaphthylamine-derived dithiol ligand.

Imidate esters can also be generated by reaction of imidoyl chlorides and allylic alcohols. The lithium anions of these imidates, prepared using lithium diethylamide, rearrange at around 0°C. When a chiral amine is used, this reaction can give rise to enantioselective formation of 7, 8-unsaturated amides. Good results were obtained with a chiral binaphthylamine.265 The methoxy substituent is believed to play a role as a Li+ ligand in the reactive enolate. 

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