An organocatalytic route to the synthesis of the atorvastatin side-chain, a building block present in the statin family, is described using L-proline-catalyzed alpha-aminooxylation of an aldehyde. The method also employs an iodine-induced intramolecular electrophilic cyclization of a carbonate to produce the iodocarbonate in a highly diastereoselective manner. (C) 2007 Elsevier Ltd. All rights reserved.
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England
Bergeron, Sophie
Chaplin, David A.
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England
Chaplin, David A.
Edwards, John H.
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Edwards, John H.
Ellis, Brian S. W.
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Ellis, Brian S. W.
Hill, Catherine L.
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Hill, Catherine L.
Holt-Tiffin, Karen
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Holt-Tiffin, Karen
Knight, Jonathan R.
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Knight, Jonathan R.
Mahoney, Thomas
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Mahoney, Thomas
Osborne, Andrew P.
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Osborne, Andrew P.
Ruecroft, Graham
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England
Bergeron, Sophie
Chaplin, David A.
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England
Chaplin, David A.
Edwards, John H.
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Edwards, John H.
Ellis, Brian S. W.
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England
Ellis, Brian S. W.
Hill, Catherine L.
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Hill, Catherine L.
Holt-Tiffin, Karen
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England
Holt-Tiffin, Karen
Knight, Jonathan R.
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England
Knight, Jonathan R.
Mahoney, Thomas
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Mahoney, Thomas
Osborne, Andrew P.
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England
Osborne, Andrew P.
Ruecroft, Graham
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Dow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, EnglandDow Chem Co USA, Dowpharma Chirotech Technol Ltd, Cambridge CB4 0WG, England