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2.4.3.4.1 Kinetic Resolution via Deamination

DOI: 10.1055/sos-SD-215-00213

Simon, R. C.; Busto, E.; Fischereder, E.-M.; Fuchs, C. S.; Pressnitz, D.; Richter, N.; Kroutil, W.Science of Synthesis: Biocatalysis in Organic Synthesis, (20152413.

Enantiopure monocyclic amines can be accessed by kinetic resolution via deamination of the racemic amines catalyzed by ω-transaminases. For instance, optically pure pyrrolidin-3-amines 28 (n = 1) and piperidin-3-amines 28 (n = 2) are successfully prepared using such an enzyme-catalyzed strategy. The cyclic amines are attractive synthons for the preparation of a broad range of biologically active pharmaceuticals.[‌80‌‌84‌] Whereas alternative chemical strategies such as substitution, cyclization, and classical resolution of the racemate with a resolving agent often include multiple steps or lack in selectivity, a kinetic resolution catalyzed by a very selective enzyme is a powerful alternative route.

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