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Preparation of planar‐chiral multidonor phosphanylferrocene carboxamides and their application as ligands for palladium‐catalysed asymmetric allylic alkylation
Author(s) -
Lamač Martin,
Tauchman Jiří,
Dietrich Sascha,
Císařová Ivana,
Lang Heinrich,
Štěpnička Petr
Publication year - 2010
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.1616
Subject(s) - chemistry , tsuji–trost reaction , palladium , ferrocene , carbodiimide , amide , alkylation , malonate , dimethyl malonate , allylic rearrangement , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry , electrode , electrochemistry
Amide coupling of ( S p )‐2‐(diphenylphosphanyl)ferrocene‐1‐carboxylic acid with appropriate terminal amines mediated by 1‐hydroxybenzotriazole and a carbodiimide affords multi‐donor amides terminally functionalized with planar‐chiral ( S p )‐2‐(diphenylphosphanyl)ferrocen‐1‐yl moieties in good to excellent yields. Palladium catalysts based on these ligands efficiently promote asymmetric allylic alkylation of 1,3‐diphenylallyl acetate with in situ generated dimethyl malonate anion to give the C‐alkylated product with ees up to 93% at room temperature. Copyright © 2010 John Wiley & Sons, Ltd.