Chiral Hemilabile P,N-Ligand-Assisted Gold Redox Catalysis for Enantioselective Alkene Aminoarylation.

Ye, Xiaohan; Wang, Chenhuan; Zhang, Shuyao; Tang, Qi; Wojtas, Lukasz; Li, Minyong; Shi, Xiaodong

Ye, Xiaohan; Wang, Chenhuan; Zhang, Shuyao; Tang, Qi; Wojtas, Lukasz; Li, Minyong; Shi, Xiaodong.

Ye X; Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.
Wang C; Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.
Zhang S; Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.
Tang Q; Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.
Wojtas L; Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.
Li M; Department of Medicinal Chemistry, Key Laboratory of Chemical Biology(MOE), School of Pharmacy, Cheeloo College of Medicine, Shandong University, Jinan, Shandong, 250012, P. R. China.
Shi X; Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.

Chemistry ; 28(34): e202201018, 2022 Jun 15.

Article en En | MEDLINE | ID: mdl-35420241

ABSTRACT

ABSTRACT

Enantioselective, intermolecular alkene arylamination was achieved through gold redox catalysis. Screening of ligands revealed chiral P,N ligands as the optimal choice, giving alkene aminoarylation with good yields (up to 80 %) and excellent stereoselectivity (up to 99 1 er). As the first example of enantioselective gold redox catalysis, this work confirmed the feasibility of applying a chiral ligand at the gold(I) stage, with the stereodetermining step (SDS) at the gold(III) intermediate, thus opening up a new way to conduct gold redox catalysis with stereochemistry control.

Asunto(s)

Alquenos; Oro; Alquenos/química; Catálisis; Oro/química; Ligandos; Oxidación-Reducción; Estereoisomerismo

Palabras clave

alkenes; enantioselectivity; gold catalysis; hemilabile ligand; redox chemistry

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