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Preparation of planar‐chiral multidonor phosphanylferrocene carboxamides and their application as ligands for palladium‐catalysed asymmetric allylic alkylation |
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| Authors: | Martin Lamač Jiří Tauchman Sascha Dietrich Ivana Císařová Heinrich Lang Petr Štěpnička |
| Affiliation: | 1. Charles University in Prague, Faculty of Science, Department of Inorganic Chemistry, Hlavova 2030, 128 40 Prague, Czech Republic;2. Chemnitz University of Technology, Faculty of Natural Sciences, Institute of Chemistry, Department of Inorganic Chemistry, Stra?e der Nationen 62, 09111 Chemnitz, Germany |
| Abstract: | Amide coupling of (Sp)‐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 (Sp)‐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. |
| Keywords: | ferrocene phosphanes carboxamides PAMAM palladium asymmetric allylic alkylation |