One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines
Sam Mathew, Arunachalam Sagadevan, Dominik Renn, Magnus Rueping
Abstract
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%.
Topics & Concepts
Yield (engineering)AlkyneEnantiomeric excessCatalysisChemistryEnantiomerOrganic chemistryBiocatalysisCombinatorial chemistryTransaminaseEnantioselective synthesisEnzymeMaterials scienceReaction mechanismMetallurgyEnzyme Catalysis and ImmobilizationCatalytic Alkyne ReactionsAsymmetric Hydrogenation and Catalysis