Asymmetric ring opening of epoxides with cyanides catalysed by chiral binuclear titanium complexes |
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| Institution: | 1. Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain;2. Catalan Institute of Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona, Spain;1. Program of Postgraduate in Chemistry, Federal University of Ceará, Pici Campus, Science Center, Fortaleza, CE, CEP: 60455-760, Brazil;2. Federal Institute of Education, Science and Technology of Rio Grande do Norte, Campus Apodi, RN, CEP: 59700-000, Brazil;3. Federal Institute of Education, Science and Technology of Ceará, Campus Acaraú, CE, CEP 62580-000, Brazil;4. University of International Integration Lusofonia Afro-Brasileira – UNILAB, Campus das Auroras, Redenção, CE, CEP: 62790-970, Brazil;1. Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 boulevard du Maréchal Juin, 14050 Caen, France;2. Unité de Recherche en Chimie Organique et Macromoléculaire, Faculté des Sciences et Techniques de l’Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France;1. Department of Chemistry, University of Louisville, Louisville, KY 40292, United States;2. Department of Chemistry and Physics, Bellarmine University, Louisville, KY 40205, United States;3. College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China |
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| Abstract: | A series of Schiff bases obtained from salicylaldehydes and 3,3′-diformyl-BINOL were synthesized. The complexes of these Schiff bases with Ti(IV) were active for the asymmetric ring opening of epoxides with TMSCN. A mixture of unpurified ligands was found to be as effective as the best one. The influence of temperature, solvent polarity and structural modification of the pre-catalysts on the enantioselectivity of the process has also been investigated. |
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