Enamines: efficient nucleophiles for the palladium-catalyzed asymmetric allylic alkylation |
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Authors: | Xiaohu Zhao |
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Institution: | School of Chemistry and Chemical Technology, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, PR China |
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Abstract: | Enamines were tested to be efficient nucleophiles for palladium-catalyzed asymmetric allylic alkylation, avoiding the use of unstablilized ketone enolates formed by strong bases. The influence of the chiral metallocene-based ligands upon this reaction was studied in detail. It was shown that planar chirality played an important role in enantioselectivities. Meanwhile, different kinds of enamines and allylic acetate to the reactions were also investigated. High catalytic activity and excellent enantioselectivity (up to 99% ee) were obtained with pyrrolidine enamines of both aliphatic and aromatic ketone. |
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Keywords: | Enamines Planar chirality Chiral ligands Palladium-catalyzed Asymmetric allylic alkylation |
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