Kinetic resolution of primary alcohols having remote stereogenic centers: lipase mediated kinetic resolution of (±)-3-chloro-3-arylpropanols |
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| Institution: | 1. Medical Oncology Service, Hospital Universitario 12 de Octubre, Avda de Córdoba S/N, 28041 Madrid, Spain;2. Instituto de Investigación Hospital 12 de Octubre, Avda de Córdoba S/N, 28041 Madrid, Spain;3. Inorganic Chemistry Department (Módulo 7), Universidad Autónoma de Madrid, C/Fco Tomás y Valiente, 5, Cantoblanco, 28049 Madrid, Spain;4. Organic Chemistry Department (Módulo 1), Universidad Autónoma de Madrid, C/Fco Tomás y Valiente, 5, Cantoblanco, 28049 Madrid, Spain;1. Department of Chemistry, Queensborough Community College of the City University of New York, 222-05 56th Ave., Bayside, NY 11364, USA;2. Department of Natural Sciences, Baruch College of the City University of New York, 17 Lexington Ave., New York, NY 10010, USA;3. Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Flushing, NY 11367, USA;1. Natural Compounds Chemistry Department, National Research Centre, Dokki, 12311 Cairo, Egypt;2. Phytochemistry Department, National Research Centre, Dokki, 12311 Cairo, Egypt;3. Faculty of Pharmaceutical Sciences, University Paul Sabatier Toulouse III, 31062 Toulouse, France;4. Department of Pathology, National Research Centre, Dokki, 12311 Cairo, Egypt;1. Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, 43210, United States;2. Catalytic Chemistry Research Unit, Department of Chemistry, King Mongkut''s Institute of Technology Ladkrabang, Bangkok, 10520, Thailand;3. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK;1. Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Sorbonne Universités, UPMC Univ Paris 06, 4 Place Jussieu, CC 229, F-75005 Paris, France;2. Ecole Normale Supérieure – PSL Research University, Département de Chimie, Sorbonne Universités, UPMC Univ Paris 06, CNRS UMR 8640 PASTEUR, 24 Rue Lhomond, F-75231 Paris, Cedex 05, France |
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| Abstract: | Kinetic resolutions of (±)-3-chloro-3-arylpropanols by lipase mediated acetylation are described for the first time. Acetylation with CCL provided the best enantioselectivity amongst the enzymes used. Enantiomerically enriched products were obtained with up to 78% ee after two successive lipase-catalyzed acetylations. Different substituents on the aromatic ring and bromide, instead of chloride, on the substrates were found to have no drastic influence on the enantioselectivity of the reaction. |
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