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Construction of Quaternary Carbon Center by Catalytic Asymmetric Alkylation of 3‐Arylpiperidin‐2‐ones Under Phase‐Transfer Conditions
Author(s) -
Inukai Tomoaki,
Kano Taichi,
Maruoka Keiji
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913518
Subject(s) - alkylation , enantioselective synthesis , quaternary carbon , catalysis , yield (engineering) , chemistry , phase (matter) , carbon fibers , nitrogen , carbon atom , group (periodic table) , nitrogen atom , combinatorial chemistry , organic chemistry , materials science , ring (chemistry) , metallurgy , composite material , composite number
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.