Magnesium‐Catalyzed Asymmetric Thia‐Michael Addition to α,β‐Unsaturated Ketones

We demonstrate the application of chiral magnesium complexes in an asymmetric carbon‐sulfur bond‐forming reaction. Enantioselective and cost‐effective methodology under mild condition for the thia‐Michael addition, utilizing an in situ generated chiral dinuclear magnesium‐ProPhenol complex, has been...

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Veröffentlicht in:Advanced synthesis & catalysis 2024-03, Vol.366 (6), p.1412-1421
Hauptverfasser: Jaszczewska‐Adamczak, Joanna A., Baczewska, Paulina, Bujok, Robert, Mlynarski, Jacek
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Sprache:eng
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Zusammenfassung:We demonstrate the application of chiral magnesium complexes in an asymmetric carbon‐sulfur bond‐forming reaction. Enantioselective and cost‐effective methodology under mild condition for the thia‐Michael addition, utilizing an in situ generated chiral dinuclear magnesium‐ProPhenol complex, has been developed. The versatility of this protocol is demonstrated with a broad range of thiol nucleophiles and a wide selection of enones. Enantioenriched β‐ketosulfides are obtained in good to excellent yields and moderate to excellent enantioselectivity. The presented catalytic system exhibits excellent tolerance for structurally different substrates while maintaining high enantioselectivity. This observation aligns with proposed mechanism, wherein the sulfur atom coordinates to the catalyst in close proximity to the reaction center.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301414