Merging Gold(I) Catalysis with Amine Transaminases in Cascade Catalysis: Chemoenzymatic Transformation of Propargylic Alcohols into Enantioenriched Allylic Amines

The compatibility between gold(I) catalysts and amine transaminases has been explored to transform racemic propargylic alcohols into enantioenriched allylic amines in a straightforward selective manner. synthetic approach consists of gold(I)-catalysed Meyer-Schuster rearrangement series 2-arylpent-3-yn-2-ols subsequent stereoselective enzyme-catalysed transamination the resulting α,β-unsaturated prochiral ketones. design cascade processes involving sequential or concurrent approaches studied our search for ideal reaction conditions produce desired amines. Thus, N-heterocyclic carbene complex [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-[bis(trifluoromethanesulfonyl)-imide]gold(I) ([Au(IPr)(NTf2)] (A) aqueous medium was found be an catalyst, while selective, made-in-house commercial permitted asymmetric synthesis both (E)-4-arylpent-3-en-2-amine enantiomers good isolated yields (53–84%) excellent stereoselectivities (97 >99% enantiomeric excess).