Mild Direct Remote Hydroxylation of Enals in Air
Fernanda Liu, Alessandro Vicidomini, Stacey E. Brenner-Moyer
TL;DR
A new method uses air to add hydroxyl groups to specific aldehydes, which could be useful in drug development.
Contribution
A mild and selective hydroxylation method using air as the oxidant for enals with acidic γ-carbons.
Findings
Remote hydroxylation of enals using air achieves up to 80% yield.
The method selectively targets enals with acidic γ-carbons.
A catalytic enantioselective γ-hydroxylation of an enal was successfully demonstrated.
Abstract
A mild direct remote hydroxylation of α,β-unsaturated aldehydes is reported. Air is the oxidant, and tertiary alcohol products are generated in up to 80% yield. This method selectively hydroxylates enals with acidic γ-carbons and therefore may be suitable for late-stage installation of remote hydroxyl groups on medicinal aldehydes. Mechanistic studies that enabled the development of this transformation are described, as is the first example of catalytic enantioselective γ-hydroxylation of an enal.
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Taxonomy
TopicsCatalytic C–H Functionalization Methods · Asymmetric Hydrogenation and Catalysis · Advanced Synthetic Organic Chemistry