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Scandium(III) Triflate Catalyzed Direct Cyclization of Ketoamides for the Synthesis of 3‐Hydroxy‐2‐Oxindoles
Author(s) -
Wang HongLi,
Li YaMin,
Wang GangWei,
Zhang Heng,
Yang ShangDong
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300057
Subject(s) - chemistry , trifluoromethanesulfonate , scandium , intramolecular force , friedel–crafts reaction , nucleophile , reagent , catalysis , aryl , alkylation , medicinal chemistry , organic chemistry , dimethoxyethane , alkyl , electrode , electrolyte
Not so scand‐alous : We report a scandium(III) triflate catalyzed intramolecular Friedel–Crafts alkylation for the synthesis of 3‐hydroxy‐2‐oxindoles. In comparison with nucleophilic conjugate additions of organometallic or electron‐rich reagents to isatins and intramolecular addition of aryl chlorides to ketoamides, this protocol is simple, produces less waste, and omits organometallic reagents and halogenations. Bn=benzyl; DME=1,2‐dimethoxyethane.