Enantioselective α-Arylation of Ketones via a Novel Cu(I)–Bis(phosphine) Dioxide Catalytic System | Zendy

Margarita EscuderoCasao | Zendy; Giulia Licini | Zendy; Manuel Orlandi | Zendy

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Enantioselective α-Arylation of Ketones via a Novel Cu(I)–Bis(phosphine) Dioxide Catalytic System

Author(s) -

Margarita EscuderoCasao,

Giulia Licini,

Manuel Orlandi

Publication year - 2021

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.0c13236

Subject(s) - chemistry , phosphine , enol , catalysis , enantioselective synthesis , enantiomeric excess , enantiomer , palladium , combinatorial chemistry , ligand (biochemistry) , organic chemistry , biochemistry , receptor

A novel catalytic system based on copper(I) and chiral bis(phosphine) dioxides is described. This allows the arylation of silyl enol ethers to access enolizable α-arylated ketones in good yields and enantiomeric excess up to 95%. Noncyclic ketones are amenable substrates with this method, which complements other approaches based on palladium catalysis. Optimization of the ligand structure is accomplished via rational design driven by correlation analysis. Preliminary mechanistic hypotheses are also evaluated in order to identify the role of chiral bis(phosphine) dioxides.

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