Asymmetric Construction of Alkaloids Employing a Key ω-Transaminase Cascade

Taday, Freya, Ryan, James, Argent, Stephen P, Caprio, Vittorio ORCID: https://orcid.org/0000-0002-9752-6513, Maciá, Beatriz and O'Reilly, Elaine (2020) Asymmetric Construction of Alkaloids Employing a Key ω-Transaminase Cascade. Chemistry - A European Journal, 26 (17). pp. 3729-3732. ISSN 0947-6539

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Abstract

An ω‐transaminase triggered intramolecular aza‐Michael reaction has been employed for the preparation of cyclic β‐enaminones in good yield and excellent enantio‐ and diastereoselectivity, starting from easily accessible prochiral ketoynones and commercially available enzymes. The powerful thermodynamic driving force associated with the spontaneous aza‐Michael reaction effectively displaces the transaminase reaction equilibrium towards product formation, using only two equivalents of isopropylamine. To demonstrate the potential of this methodology, we have combined this biocatalytic aza‐Michael step with annulation chemistry, affording unique stereo‐defined fused alkaloid architectures.

Item Type:	Article
Peer-reviewed:	Yes
Date Deposited:	07 Feb 2020 15:21
Publisher:	Wiley
Additional Information:	This is an Author Accepted Manuscript of an article published in Chemistry - A European Journal by Wiley.
Divisions:	Faculties > Science and Engineering
Subject terms:	Annulation, Aza-Michael, Biocatalytic cascade, Ketoynone, Transaminase, General Chemistry, 03 Chemical Sciences
URI:	https://e-space.mmu.ac.uk/id/eprint/625055
DOI:	https://doi.org/10.1002/chem.202000067
ISSN	0947-6539

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