Transaminase triggered aza-Michael approach for the enantioselective synthesis of piperidine scaffolds

Ryan, James and Šiaučiulis, Mindaugas and Gomm, Andrew and Macia, Beatriz and O'Reilly, Elaine and Caprio, Vittorio (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 1520-5126

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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-TA-mediated 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.

Item Type: Article
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1021/jacs.6b07024
Depositing User: Bramwell, Roseanna
Date Deposited: 09 Jan 2017 14:35
Last Modified: 10 Jan 2017 08:58
URI: http://eprints.nottingham.ac.uk/id/eprint/39699

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