Enantioselective alpha-amination enabled by a BINAM-derived phase-transfer catalyst

Chiral anion phase-transfer of aryldiazonium cations was utilized to achieve highly enantioselective alpha-amination of carbonyl compounds. A broad scope of indanone-and benzosuberone-derived substrates was amenable to this strategy. Critical to obtaining high levels of enantioselectivity was the use of BINAM-derived phosphoric acids. The utility of this transformation was demonstrated through facile conversion of diazene products to valuable alpha-amino acid derivatives.