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The rational design of modified Cinchona alkaloid catalysts. Application to a new asymmetric synthesis of chiral chromanes |
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| Authors: | Alain Merschaert Pieter Delbeke Georges Dive |
| Institution: | a Global Chemical Product Research & Development, Lilly Research Laboratories, Lilly Development Centre S.A., Rue Granbonpré 11, B-1348 Mont-Saint-Guibert, Belgium b Service de Chimie Organique, Faculté des Sciences, Université Libre de Bruxelles, Av. F.D. Roosevelt 50, B-1050 Bruxelles, Belgium c Centre d’Ingéniérie des Protéines, Université de Liège, Bâtiment B6, Allée de la Chimie 3, B-4000 Liège, Belgium |
| Abstract: | A new asymmetric synthesis of 2-substituted chiral chromanes has been achieved. The key step is the intramolecular conjugate addition of a phenolic nucleophile on a α,β-unsaturated ester catalyzed by Cinchona alkaloids. The high ee’s obtained with cinchonine and its derivatives have been rationalized by ab initio quantum chemistry calculations of transition state structures. |
| Keywords: | Alkaloids oxa-Michael Asymmetric Catalysis |
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