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Enantioselective α‐Arylation of Cyclic β‐Ketoamides with a Quinone Monoimine
Author(s) -
Hu XiaoYan,
Hu FangZhi,
Chen Hui,
Xu XiaoYing,
Yuan WeiCheng,
Zhang XiaoMei
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800085
Subject(s) - enantioselective synthesis , bifunctional , thiourea , quinone , chemistry , amine gas treating , organic chemistry , catalysis , cyclic amines
A facile and direct method for the construction of enantioenriched α‐arylated quaternary β‐ketoamides was developed. By employing a chiral bifunctional thiourea‐tertiary amine as catalyst, enantioselective α‐arylation of cyclic β‐ketoamides with a quinone monoimine proceeded smoothly to afford various α‐arylated quaternary β‐ketoamides in good yields (up to 97%) with moderate to good enantioselectivities (up to 85% ee). Generally, benzo six‐membered cyclic β‐ketoamides exhibited better enantioselection than benzo five‐membered cyclic β‐ketoamides.