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Multi-Catalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols

preprint
submitted on 25.02.2021, 16:54 and posted on 26.02.2021, 13:34 by Alessandra Casnati, Dawid Lichosyt, Bruno Lainer, Lukas Veth, Pawel Dydio
One-pot multi-step procedures bear the potential to rapidly build up molecular complexity while avoiding the wasteful and costly isolations and purifications of consecutive intermediates. Here we report multi-catalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Because each transformation of the sequence is executed by an independent catalyst, without any catalytic cross-reactivity, allylic alcohols bearing a prochiral double bond can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er and >20:1 dr). Overall, with the aid of up to four catalysts operating in a single vessel, the protocols directly convert simple starting materials into a range of value-added products with high stereocontrol and excellent material efficiency, demonstrating both the efficacy and the advantages of the one-pot synthesis employing multiple transition-metal catalysts.

Funding

European Research Council (ERC Starting Grant # 804106)

French National Research Agency (ANR IdEx, ANR LabEx „Chemistry of Complex Systems“)

French National Research Agency (Programme d’ Investissement d’ Avenir under contract 17-EURE-0016)

History

Email Address of Submitting Author

dydio@unistra.fr

Institution

ISIS UMR 7006, University of Strasbourg & CNRS

Country

France

ORCID For Submitting Author

0000-0001-5095-4943

Declaration of Conflict of Interest

None

Exports