Rh-Mediated Asymmetric-Transfer Hydrogenation of 3‑Substituted Chromones: A Route to Enantioenriched cis-3-(Hydroxymethyl)chroman-4-ol Derivatives through Dynamic Kinetic Resolution

Enantioenriched cis-3-(hydroxymethyl)­chroman-4-ol derivatives were conveniently prepared by rhodium-catalyzed asymmetric transfer hydrogenation of 3-formylchromones through a dynamic kinetic resolution process. The reaction proceeded under mild conditions using a low catalyst loading and HCO2H/Et3N...

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Veröffentlicht in:Organic letters 2019-05, Vol.21 (9), p.3276-3280
Hauptverfasser: He, Bin, Phansavath, Phannarath, Ratovelomanana-Vidal, Virginie
Format: Artikel
Sprache:eng
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Zusammenfassung:Enantioenriched cis-3-(hydroxymethyl)­chroman-4-ol derivatives were conveniently prepared by rhodium-catalyzed asymmetric transfer hydrogenation of 3-formylchromones through a dynamic kinetic resolution process. The reaction proceeded under mild conditions using a low catalyst loading and HCO2H/Et3N (5:2) as the hydrogen source, delivering the reduced compounds in good yields, high diastereomeric ratio (up to 98:2 dr), and excellent enantioselectivities (up to >99% ee).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01002