Correction for 'Dearomatization of benzopyrylium triflates with sulfoxonium ylides' by Alexandria N. Leveille , , 2022, , 12600-12603, https://doi.org/10.1039/D2CC02023H.
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http://dx.doi.org/10.1039/d3cc90024j | DOI Listing |
Synthesis (Stuttg)
October 2022
Worcester Polytechnic Institute, Worcester, MA 01609.
A catalytic and highly enantioselective dearomative alkynylation of chromanones has been discovered that enables the construction of biologically relevant tertiary ether stereogenic centers. This methodology is robust, accommodating a variety of alkynes and chromanones. More than 40 substrates tested gave rise to >90% ee.
View Article and Find Full Text PDFChem Commun (Camb)
January 2023
Department of Chemistry and Biochemistry, Worcester Polytechnic Institute, 100 Institute Road, Worcester, MA, 01609, USA.
Correction for 'Dearomatization of benzopyrylium triflates with sulfoxonium ylides' by Alexandria N. Leveille , , 2022, , 12600-12603, https://doi.org/10.
View Article and Find Full Text PDFChem Commun (Camb)
November 2022
Department of Chemistry and Biochemistry, Worcester Polytechnic Institute, 100 Institute Road, Worcester, MA, 01609, USA.
Benzopyrylium triflates react with sulfoxonium ylides to give rise to cyclopropanated products in up to 90% yield as a single diastereomer. The cyclopropanated products can easily undergo acid-mediated ring-expansion to afford benzo[]oxepines. Control over the absolute stereochemistry of the process is possible when the reaction is executed under the influence of a suitable anion-binding catalyst.
View Article and Find Full Text PDFACS Catal
May 2021
Department of Chemistry and Biochemistry, Worcester Polytechnic Institute, 60 Prescott St., Worcester, MA 01609.
A robust, catalytic enantioselective method to construct challenging, biologically relevant, tertiary ether stereocenters has been developed. The process capitalizes on readily accessible bis(oxazoline) ligands to control the facial selectivity of the addition of copper acetylides to benzopyrylium triflates, reactive species generated in situ. Up to 99% enantiomeric excesses are achieved with a broad substrate scope.
View Article and Find Full Text PDFOrg Lett
August 2016
Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, United States.
Promising levels of enantiocontrol are observed in the silanediol-catalyzed addition of silyl ketene acetals to benzopyrylium triflates. This rare example of enantioselective, intermolecular chromenone functionalization with carbonyl-containing nucleophiles has potential applications in the synthesis of bioactive chromanones and tetrahydroxanthones.
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