Novel chiral bis(oxazolines): synthesis and application as ligands in the copper-catalyzed enantioselective conjugate addition of diethylzinc to enones |
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| Affiliation: | 1. Departamento de Química (REQUIMTE), Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Monte de Caparica, Portugal;2. Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Rua da Quinta Grande 6, Apartado 127, 2780 Oeiras, Portugal;1. The Scientific Technological Center of Organic and Pharmaceutical Chemistry, Armenian Academy of Science, Institute of Fine Organic Chemistry of A.L.Mnjoyan, Yerevan 0014, Ave. Azatutyan 26, Armenia;2. Molecular Structure Research Center of the Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan 0014, Ave. Azatutyan 26, Armenia |
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| Abstract: | Novel chiral C2-symmetric bis(oxazolines) were prepared from tartaric acid. They were applied as ligands in the copper-catalyzed conjugate addition of diethylzinc to chalcone and 2-cyclohexenone. Maximum enantiomeric excesses of 50% and 53% were obtained, respectively. The sense of induction was found to depend on the configuration of the stereogenic centre in the oxazoline ring, and not on the stereogenic centres of the 1,4-dioxane backbone. |
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