Transaminases as suitable catalysts for the synthesis of enantiopure β,β-difluoroamines?

Organic & Biomolecular Chemistry Pub Date: 2022-01-08 DOI: 10.1039/D1OB02346B

Abstract

Transaminases have shown the ability to catalyze the amination of a series of aliphatic and (hetero)aromatic α,α-difluorinated ketones with high stereoselectivity, thus providing the corresponding β,β-difluoroamines in high isolated yields (55–82%) and excellent enantiomeric excess (>99%). It was also observed that these activated substrates could be quantitatively transformed by employing a small molar excess of the amine donor since this amination process was thermodynamically favored. Selected transformations could be scaled up to 500 mg, showing the robustness of this methodology.

Graphical abstract: Transaminases as suitable catalysts for the synthesis of enantiopure β,β-difluoroamines
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