Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds

Ryan, J, Šiaučiulis, M, Gomm, A, Maciá, B, O’Reilly, E and Caprio, V (2016) Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds. Journal of the American Chemical Society, 138 (49). pp. 15798-15800. ISSN 0002-7863

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Abstract

The expanding “toolbox” of biocatalysts opens new opportunities to redesign synthetic strategies to target molecules by incorporating a key enzymatic step into the synthesis. Herein, we describe a general biocatalytic approach for the enantioselective preparation of 2,6-disubstituted piperidines starting from easily accessible pro-chiral ketoenones. The strategy represents a new biocatalytic disconnection, which relies on an ω-TAmediated aza-Michael reaction. Significantly, we show that the reversible enzymatic process can power the shuttling of amine functionality across a molecular framework, providing access to the desired aza-Michael products.