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

Add time:07/12/2019    Source:sciencedirect.com

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 ZnI2 & BF3·OEt2 and N-(−)-α-methylbenzyl substituents via double stereo differentiation.

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