Enantioselective Hydrocyanation of N-Protected Aldimines.

Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly]2[(S)-binap]/C6H5OLi system or a bimetallic complex [Li{Ru[(S)-phgly]2[(S)-binap]}]Cl affords the amino nitriles in 92–99% ee. The reaction is carried out in tert-C4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500–5000 at −20 to 0 °C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.