One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, with ee > 99%.

Automated summary

A one-pot chemoenzymatic sequential cascade was developed for the synthesis of chiral amines from alkynes. Gold catalysts were used to convert alkynes to ketones, followed by a transaminase catalyzed production of chiral amines with high yields and enantiomeric excess. Preparative scale synthesis of specific chiral amines showed high yields and enantiomeric excess.