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Chiral ytterbium silylamide catalyzed enantioselective phospha-Michael addition of diethyl phosphite to chalcones
Affiliation:1. Laboratorio de Química Orgánica, Departamento de Química Orgánica, Facultad de Química—Universidad de la República, General Flores 2124, 11800 Montevideo, Uruguay;2. Cátedra de Química Inorgánica, Departamento Estrella Campos, Facultad de Química—Universidad de la República, General Flores 2124, 11800 Montevideo, Uruguay;1. MTA-BME Research Group for Organic Chemical Technology, 1521 Budapest, Hungary;2. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary;3. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany;4. Department of Inorganic Chemistry, University of Pécs and Szentágothai Research Center, 7624 Pécs, Hungary;5. MTA-PTE Research Group for Selective Chemical Syntheses, H-7624 Pécs, Ifjúság u. 6., Hungary;1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, 1521 Budapest, Hungary;2. MTA-BME Lendület Quantum Chemistry Research Group, Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, 1521 Budapest, Hungary;3. Institute of Materials and Environmental Chemistry, Research Center for Natural Sciences, Hungarian Academy of Sciences, 1519 Budapest, P.O. Box 286, Hungary;4. Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, P.O. Box 91, 1521 Budapest, Hungary;1. A.M. Butlerov Institute of Chemistry, Kazan Federal University, Kremlevskaya Street, 18, Kazan, 420008, Russian Federation;2. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Street, 8, Kazan, 420088, Russian Federation;1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmans’ka str., Kyiv 02660, Ukraine;2. Department of Organic Chemistry, National Technical University of Ukraine ‘Kyiv Polytechnic Institute’, 37, Prospect Peremogy, Kyiv 03056, Ukraine
Abstract:An efficient and enantioselective phospha-Michael addition of diethyl phosphite to chalcones has been established. In the presence of a catalytic amount of chiral lanthanide silylamide generated from [(Me3Si)2N]3Yb(μ-Cl)Li(THF)3 and salen, the reaction produced the target γ-oxophosphonates with high yields and enantioselectivity.
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