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Axially dissymmetric N ‐thioacylated ( S )‐(–)‐1,1′‐binaphthyl‐2,2′‐diamine ligands for copper‐catalyzed asymmetric Michael addition of diethylzinc to α,β‐unsaturated ketone
Author(s) -
Shi Min,
Duan WeiLiang,
Rong GuoBin
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20086
Subject(s) - chemistry , diethylzinc , thioamide , ligand (biochemistry) , diamine , chirality (physics) , catalysis , ketone , copper , michael reaction , medicinal chemistry , stereochemistry , enantioselective synthesis , organic chemistry , receptor , biochemistry , physics , quantum mechanics , quark , nambu–jona lasinio model , chiral symmetry breaking
Abstract Axially chiral thioamide ligands L5, L6, L8, L11, and bis(thioamide) ligand L13 were prepared from the reaction of ( S )‐(–)‐1,1′‐binaphthyl‐2,2′‐diamine with acyl chlorides and phosphorus pentasulfide (P 2 S 5 ). The catalytic asymmetric 1,4‐addition of diethylzinc to α,β‐unsaturated ketones was examined using this novel chiral ligand system with 28–73% ee in moderate to good yields. Chirality 16:642–651, 2004. © 2004 Wiley‐Liss, Inc.