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Synthesis of chiral 2-alkyl-8-quinolinyl-oxazoline ligands: reversal of enantioselectivity in the asymmetric palladium-catalyzed allylic alkylation |
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| Authors: | Xiao-Guang Li Xu Cheng Jun-An Ma Qi-Lin Zhou |
| Affiliation: | a The State Key Laboratory and the Institute of Elemento-organic Chemistry, Nankai University, Weijin Road 94, Tianjin 300071, People's Republic of China b The Open Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People's Republic of China |
| Abstract: | New chiral 2-alkyl-8-quinolinyl-oxazolines were synthesized from 2-alkyl-8-quinolinecarboxylic acids and enantiomerically pure amino alcohols using a convenient procedure. Enantioselective palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate in the presence of 2-alkyl-8-quinolinyl-oxazolines provided an alkylation product with an opposite configuration compared to those obtained from unsubstituted quinolinyl-oxazoline ligands. |
| Keywords: | Palladium complexes Asymmetric catalysis Chiral ligands Allylic alkylation |
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