Stereoselective Nucleophilic Addition with a New Chiral Template and Its Application to the Synthesis of Optically Active α-Arylglycine Derivatives

Mannich-type reaction of phenols with iminolactone 4, readily prepared from commercially available phenylglycine, proceeded with high stereoselectivity to give α-arylglycine derivatives. The reaction was also applicable to other electron-rich aromatic compounds, arylboronic acids and other nucleophiles. Additionally, several Lewis acid-promoted addition reactions with iminolactone 4 were accomplished efficiently. These adducts could be converted readily to the corresponding optically active α-amino acid derivatives.