title: Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds.
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.
authors.affiliation: Faculty of Science & Engineering, Division of Chemistry & Environmental Science, Manchester Metropolitan University , Chester Street, Manchester M1 5GD, United Kingdom.
authors.forename: James
authors.initials: J
authors.lastname: Ryan
authors.affiliation: School of Chemistry, University of Nottingham , University Park, Nottingham NG7 2RD, United Kingdom.
authors.forename: Mindaugas
authors.initials: M
authors.lastname: Šiaučiulis
authors.affiliation: School of Chemistry, University of Nottingham , University Park, Nottingham NG7 2RD, United Kingdom.
authors.forename: Andrew
authors.initials: A
authors.lastname: Gomm
authors.affiliation: Faculty of Science & Engineering, Division of Chemistry & Environmental Science, Manchester Metropolitan University , Chester Street, Manchester M1 5GD, United Kingdom.
authors.forename: Beatriz
authors.initials: B
authors.lastname: Maciá
authors.affiliation: School of Chemistry, University of Nottingham , University Park, Nottingham NG7 2RD, United Kingdom.
authors.forename: Elaine
authors.initials: E
authors.lastname: O'Reilly
authors.affiliation: Faculty of Science & Engineering, Division of Chemistry & Environmental Science, Manchester Metropolitan University , Chester Street, Manchester M1 5GD, United Kingdom.
authors.forename: Vittorio
authors.initials: V
authors.lastname: Caprio