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Modular amino acid amide chiral ligands for enantioselective addition of diethylzinc to aromatic aldehydes
Author(s) -
Gou Shaohua,
Ye Zhongbin,
Chang Jing,
Gou Guangjun,
Feng Mingming
Publication year - 2011
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1785
Subject(s) - diethylzinc , chemistry , enantioselective synthesis , amide , catalysis , ligand (biochemistry) , organic chemistry , alcohol , combinatorial chemistry , biochemistry , receptor
Enantioselective addition of diethylzinc to a series of aromatic aldehydes was developed using a modular amino acid amide chiral ligand (2 S )‐3‐phenyl‐ N ‐(( R )‐1‐phenyl‐ethyl)‐2‐(tosylamino)propanamide without using titanium complex. The catalytic system employing 10 mol% of 1g was found to promote the addition of diethylzinc (ZnEt 2 ) to a wide range of aromatic aldehydes with electron‐donating and electron‐withdrawing substituents, giving up to 82% ee of the corresponding secondary alcohol under mild conditions. Copyright © 2011 John Wiley & Sons, Ltd.