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Asymmetric Epoxidation of Olefins with H 2 O 2 Catalyzed by a Bioinspired Aminopyridine N4 Iron Complex
Author(s) -
Wang Wenfang,
Sun Qiangsheng,
Xu Daqian,
Xia Chungu,
Sun Wei
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201601293
Subject(s) - chemistry , morpholine , ligand (biochemistry) , catalysis , yield (engineering) , hydrogen peroxide , dabco , 2 aminopyridine , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , biochemistry , receptor , metallurgy
Abstract An iron complex with a chiral aminopyridine N4 ligand bearing strong electron‐donating and bulky morpholine groups on the ligand is synthesized and characterized. The iron complex serves to efficiently catalyze the asymmetric epoxidation of various olefins by employing aqueous hydrogen peroxide as the green oxidant, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 93 % yield and 99.9 % ee ). Owing to the introduction of morpholine functional groups on the ligand, the Fe‐catalyzed reaction can proceed with a catalytic amount of the carboxylic acid partner (3 mol %).