Merging Gold(I) Catalysis with Amine Transaminases in Cascade Catalysis: Chemoenzymatic Transformation of Propargylic Alcohols into Enantioenriched Allylic Amines
نویسندگان
چکیده
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).
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ژورنال
عنوان ژورنال: Advanced Synthesis & Catalysis
سال: 2022
ISSN: ['1615-4169', '1615-4150']
DOI: https://doi.org/10.1002/adsc.202200777