Enantiomerically pure amines are highly valuable products or building blocks for the synthesis of a broad range of biologically active compounds as pharmaceuticals and agrochemicals. The biocatalysis has been an important, useful and interesting tool to synthesize this class of molecules. On the other hand, the interests about organoboron chemistry have grown during the last decades due the versatility of these compounds. Herein, we describe the application of ?-transaminases (?-TA) as biocatalysts in the asymmetric reductive amination of boron containing ketones as alternative to prepare organoboron compounds having free amino group. The transamination reaction employing R-selective ?-TA from Arthrobacter sp. and Aspergillus terreus furnished the desired amines with high conversions (up to 94%) while the S-selective ?-TA from Chromobacterium violaceum provides the amines with conversions up to 74%. In most of cases, excellent enantiomeric excesses (>99%) were achieved. Moreover, boronic functions as acid, ester and potassium trifluoroborates were well accepted by those enzymes.

Asymmetric reductive amination of boron-containing ketones using ?-transaminases

246th National Meeting (2013)

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