Asymmetric Intramolecular Hydroamination of Allenes using Mononuclear Gold Catalysts

Abstract

The intramolecular gold-catalyzed asymmetric hydroamination of allenes was studied by screening a series of mononuclear gold(I) and -(III) complexes in combination with silver salts. Among the various chiral monophosphine and diaminocarbene ligands tried, the best catalysts arose from mononuclear gold(I) complexes synthesized from BINOL-based phosphoramidite ligands. The latest were improved by addition of bulky substituents at specific positions of the BINOL scaffold. The resulting gold(I) complexes were combined with selected silver salts to afford efficient catalysts for intramolecular hydroamination of allenes at room temperature or below, with good conversions and enantioselectivities.