Nickel-catalyzed intramolecular [4+4] cycloadditions: 2. Allylic stereoinduction and modelling studies in the preparation of bicyclo[6.4.0]dodecadienes |
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Affiliation: | 1. AstraZeneca, Centre de Recherches, Z.I. La Pompelle, B.P. 1050, Chemin de Vrilly, 51689 Reims, Cedex 2, France;2. AstraZeneca Pharmaceuticals, Oncology iMed, Alderley Park, Macclesfield, Cheshire SK10 4TG, United Kingdom;1. Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, and School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenyang 110016, PR China;2. Wuya College of Innovation, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenyang 110016, PR China;3. Shenyang Institute of Applied Ecology, Chinese Academy of Sciences, 72 Wenhua Road, Shenyang 110016, PR China;4. School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenyang 110016, PR China;5. School of Pharmaceutical Sciences, Mukogawa Women''s University, 11-68 Koshien, Nishinomiya 663-8179, Japan;1. Department of Inorganic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya 6, 79005 Lviv, Ukraine;2. Institute of Low Temperature and Structure Research, Okólna 2, 50-422 Wrocław, Poland;3. Department of Inorganic Chemistry and Technology, “Jožef Stefan” Institute, Jamova 39, 1000, Ljubljana, Slovenia;4. Department of Analytical Chemistry, Faculty of Pharmacy, Wroclaw Medical University, Borowska 211A, 50-556 Wroclaw, Poland;1. Global Discovery Chemistry, Novartis Institutes for Biomedical Research, 250 Massachusetts Avenue, Cambridge, MA 02139, USA;2. Infectious Disease Area, Novartis Institutes for Biomedical Research, 100 Technology Square, Cambridge, MA 02139, USA;1. Center of Drug Discovery, State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China;2. School of Pharmacy, Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection, Yancheng Teachers’ University, Yancheng, PR China;3. Jiangsu Key Laboratory of Drug Discovery for Metabolic Disease, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China;4. Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, PR China;1. Discovery Chemistry, Merck Research Laboratories, West Point, PA 19486, United States;2. Global Structural Chemistry, Merck Research Laboratories, West Point, PA 19486, United States;3. Pharmacokinetics, Pharmacodynamics, and Drug Metabolism, Merck Research Laboratories, West Point, PA 19486, United States;4. In Vitro Pharmacology, Merck Research Laboratories, West Point, PA 19486, United States;5. Infectious Disease Biology, Merck Research Laboratories, West Point, PA 19486, United States;6. Discovery Process Chemistry, Merck Research Laboratories, West Point, PA 19486, United States;7. Discovery Pharmaceutical Sciences, Merck Research Laboratories, West Point, PA 19486, United States;8. Merck Frost Centre for Therapeutic Research, Kirkland, QC, Canada |
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Abstract: | The extent of diastereoinduction observed in the nickel-catalyzed intramolecular [4+4] cycloaddition of tethered 1,3-dienes is shown to be highly dependent upon the steric nature of the substituents at the stereogenic center. A model for the prediction of the extent and sense of induction is presented. |
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