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Resolution of racemic 1-azido-3-aryloxy-2-propanols by lipase-catalyzed enantioselective acetylation
Affiliation:1. Laboratoire des Réactions Sélectives sur Supports (CNRS UMR 8615), Institut de Chimie Moléculaire d''Orsay, Bât. 410, Université de Paris-Sud, 91405 Orsay Cedex, France;2. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland;3. Laboratoire des Carbocycles (CNRS UMR 8615), Institut de Chimie Moléculaire d''Orsay, Bât. 420, Université de Paris-Sud, 91405 Orsay Cedex, France;1. College of Life Science, Fujian Normal University, Fuzhou 350117, China;2. Engineering Research Center of Industrial Microbiology of Ministry of Education, Fujian Normal University, Fuzhou 350117, China;3. Department of Engineering, Aarhus University, Gustav Wieds Vej 10, 8000 Aarhus C, Denmark;1. Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, Cx. P. 19046 Centro Politécnico, Curitiba 81531-980, Paraná, Brazil;2. Instituto Federal do Paraná – Campus Irati, Irati 84500-000, Paraná, Brazil;3. Departamento de Química, Universidade Federal do Paraná, Cx. P. 19081 Centro Politécnico, Curitiba 81531-980, Paraná, Brazil;4. Departamento de Engenharia Química, Universidade Estadual de Maringá, Maringá 87020-900, Paraná, Brazil;1. Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F.Stagno d’Alcontres 31, I-98166 Messina, Italy;2. Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria, 6, I-95125 Catania, Italy;3. CNR-IPCB Istituto per i Polimeri, Compositi e Biomateriali, Via P. Gaifami 18, I-95126 Catania, Italy;1. Department of Engineering, Aarhus University, Gustav WiedsVej 10, 8000 Aarhus C, Denmark;2. College of Life Science, Fujian Normal University, No.1, Keji Road, Minhou, Fuzhou 350117, China;3. Engineering Research Center of Industrial Microbiology of Ministry of Education, Fujian Normal University, No.1, Keji Road, Minhou, Fuzhou 350117, China
Abstract:Kinetic resolution of racemic 1-azido-3-aryloxy-2-propanols 1ag was performed using supported lipase of Candida antarctica-B (Novozym® SP 435) in toluene at 4°C with isopropenyl acetate as the acyl donor to afford the optically active (S)-alcohols 2ag and their corresponding (R)-acetates 3ag with E values from 56 to 72.
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