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Catalytic Asymmetric Ring‐Opening Reactions of Aziridines with 3‐Aryl‐Oxindoles
Author(s) -
Wang Linqing,
Li Dan,
Yang Dongxu,
Wang Kezhou,
Wang Jie,
Wang Pengxin,
Su Wu,
Wang Rui
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201501369
Subject(s) - aziridine , oxindole , enantioselective synthesis , aryl , catalysis , ring (chemistry) , chemistry , ligand (biochemistry) , combinatorial chemistry , alkylation , alkyl , medicinal chemistry , organic chemistry , biochemistry , receptor
A highly enantioselective ring‐opening alkylation reaction between 3‐aryl‐oxindole and N ‐(2‐ p icolinoyl) aziridine has been realized for the first time. The reaction is efficiently mediated by a simple in‐situ‐generated magnesium catalyst and 3,3′‐fluorinated‐BINOL (BINOL=1,1′‐binaphthalene‐2,2′‐diol) has been identified as a powerful chiral ligand. Notably, the fluorine atom on the chiral ligand plays a key role in providing the desired chiral 3‐alkyl‐3‐aryl oxindoles with excellent enantioselectivities.