Construction of Quaternary Carbon Center by Catalytic Asymmetric Alkylation of 3-Arylpiperidin-2-ones Under Phase-Transfer Conditions
Tomoaki Inukai
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Taichi Kano
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Keiji Maruoka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Department of Organocatalytic Chemistry, Graduate School of PharmaceuticalSciences, Kyoto University, Sakyo, Kyoto, 606-8501 Japan
Guangdong University of Technology, Guangzhou, 510006 China
School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006 China
Search for more papers by this authorTomoaki Inukai
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Taichi Kano
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Keiji Maruoka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Department of Organocatalytic Chemistry, Graduate School of PharmaceuticalSciences, Kyoto University, Sakyo, Kyoto, 606-8501 Japan
Guangdong University of Technology, Guangzhou, 510006 China
School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006 China
Search for more papers by this authorGraphical Abstract
In phase: δ-Lactams having a chiral quaternary carbon center were synthesized through an asymmetric alkylation of 3-arylpiperidin-2-ones under phase-transfer conditions. A 2,2-diarylvinyl group on the δ-lactam nitrogen atom plays a crucial role as a novel protecting group and an achiral auxiliary for improving both yield and enantioselectivity of the reaction.
Abstract
A highly enantioselective synthesis of δ-lactams having a chiral quaternary carbon center at the α-position has been developed through an asymmetric alkylation of 3-arylpiperidin-2-ones under phase-transfer conditions. In this transformation, a 2,2-diarylvinyl group on the δ-lactam nitrogen atom plays a crucial role as a novel protecting group and an achiral auxiliary for improving both yield and enantioselectivity of the reaction.
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