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Asymmetric Construction of Alkaloids Employing a Key ω-Transaminase Cascade

Taday, Freya, Ryan, James, Argent, Stephen P, Caprio, Vittorio ORCID logoORCID: 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. ISSN 0947-6539

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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.

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