Synergistic substrate and catalyst effects in the addition of trimethylsilyl cyanide to imines derived from lactic acid

Trimethylsilylcyanide was added to various imines derived from (2S)-ethyl lactate in the presence of Lewis acids to provide both syn- and anti- β-hydroxy-α-aminonitrile stereoisomers. Syn-products were found to be the major in most instances, however, anti-products were formed in good yield and selectivity in the presence of ZnI 2 & BF 3 ·OEt 2 and N-(−)-α-methylbenzyl substituents via double stereo differentiation