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A convenient route to both enantiomers of endo-2-benzonorbornenol via lipase catalysed resolution of the racemic mixture
Institution:1. Departamento de Qu??mica Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, E-15706 Santiago de Compostela, Spain;2. Departamento de Qu??mica da Faculdade de Ciências do Porto, Rua do Campo Alegre, 687-4169007 Porto, Portugal;1. Department of Optics and Photonics, Faculty of Fundamental Problems of Technology, Wroclaw University of Science and Technology, Wybrzeze Wyspianskiego 27, 50‐370 Wroclaw, Poland;2. Laboratory of Optical Fibre Technology, Maria Curie-Sklodowska University, Marii Curie‐Sklodowska Sq. 2, 20-031 Lublin, Poland;1. State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, People’s Republic of China;2. State Key Laboratory of Core Technology in Innovative Chinese Medicine, Pharmaceutical Analysis Institute, Tasly Academy, Tianjin 300410, People’s Republic of China;3. Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai 980-8578, Japan;4. Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Republic of Korea
Abstract:Resolution of racemic endo-benzonorbornenol (±)-4 was performed using Candida antarctica lipase (Novozym® 435) in benzene (50°C/50 hours) with vinyl acetate as the acyl donor to afford (?)-endo-2-benzonorbornenol (?)-6 and their corresponding (+)-endo-2-benzonorbornenyl acetate (+)-5 in high e.e.s of up to 99% and workable yields of up to 45–46%.
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