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Asymmetric palladium-catalyzed benzylic nucleophilic substitution: high enantioselectivity with the DUPHOS family ligands
Affiliation:1. State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China;2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China;3. Department of Pharmaceutical Chemistry, University of California, San Francisco, CA 94158, USA;1. The College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000, People’s Republic of China;2. The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan 450052, People’s Republic of China;1. Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, ENSTA ParisTech-UMR 7652, Université Paris-Saclay, 828 Bd des Maréchaux, 91128 Palaiseau, France;2. Laboratoire de Chimie et d’Electrochimie, Département de Chimie, Université des sciences et de la technologie d''Oran. Mohamed Boudiaf USTO-MB, BP1505,El M''nouar 31000 Oran, Algeria;1. State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China;2. School of Pharmacy, University of Otago, Dunedin 9054, New Zealand
Abstract:The asymmetric palladium-catalyzed benzylic reaction of 1-(2-naphthyl)ethyl acetate and its 6-methoxy substituted analogue with dimethyl malonate anion led to substitution products with up to 90% ee when the iPr-DUPHOS chiral ligand was used.
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