Zirconium–BINOLate-catalyzed,enantioselective aldol-Tishchenko reactions of aromatic ketone aldols |
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| Affiliation: | 1. Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China;2. College of Chemistry and Chemical Engineering, Northwest Normal University, Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Key Laboratory of Polymer Materials of Gansu Province, Lanzhou 730070, China;1. Department of Chemistry, University of North Florida, 1, UNF Drive, Jacksonville, FL 32224, USA;2. INFIQC, CONICET and Departamento de Matemática y Física, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina;1. Department of Radiology CS2, Leiden University Medical Center, Albinusdreef 2, 2333 ZA Leiden, Netherlands;2. Department of Bioorganic Synthesis, Leiden Institute of Chemistry, Leiden University, Leiden, Netherlands;3. Radionucleotide Laboratory, Free University, Amsterdam, Netherlands;4. Division of Drug Delivery Technology, Leiden Academic Center for Drug Research, Leiden University, Leiden, Netherlands;5. Department of Human Genetics, Leiden University Medical Center, Leiden, Netherlands;1. Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;2. Université de Rennes 1, Institut des Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France;1. Key Laboratory of Radiopharmaceuticals (Beijing Normal University), Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China;2. Nuclear Medicine Department, Chinese PLA General Hospital, Beijing 100853, China;3. Helmholtz-Zentrum Dresden-Rossendorf, Institute of Radiopharmaceutical Cancer Research, Department of Neuroradiopharmaceuticals, 04318 Leipzig, Germany;4. PET Center, Department of Diagnostic Radiology, Yale University School of Medicine, New Haven, CT, USA |
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| Abstract: | 3,3′-Substituted BINOL’s have been identified as suitable chiral ligands for the zirconium-catalyzed aldol-Tishchenko reaction of aromatic ketone aldols with aliphatic aldehydes. 1,3-anti-Diol monoesters were obtained in excellent yields, complete anti-diastereocontrol, and enantioselectivities of up to 60% ee. |
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