Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones. (18th July 2022)

• Record Type: Journal Article
• Authors: Solas, Marta; Suárez‐Pantiga, Samuel; Sanz, Roberto
• Is Part Of: Angewandte Chemie. Volume 134:Number 35(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-07-18
• Subjects: Asymmetric Catalysis -- Cyclopentenones -- Gold -- Hydroarylation -- Nazarov Cyclization; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202207406
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The asymmetric synthesis of cyclopentachromenones from gold‐catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti ‐Michael hydroarylation of the ynone moiety to form a gold‐functionalized dialkenylketone intermediate, followed by a Nazarov cyclization that proceeds in an unprecedented enantioselective manner. Excellent enantiomeric ratios and chemical yields are obtained under mild reaction conditions. Abstract : A new enantioselective version of the Nazarov cyclization is reported. The reaction design uses readily available alkenynones to trigger a gold(I)‐catalyzed anti ‐Michael hydroarylation of the ynone followed by Nazarov cyclization. A chiral gold complex is able to control the absolute stereochemistry of the process. Cyclopenta[ c ]chromenones, which combine the 2 H ‐chromene and cylopentanone cores, are synthesized with high yields and ee values.