Boron‐Catalyzed Regioselective Deoxygenation of Terminal 1,2‐Diols to 2‐Alkanols Enabled by the Strategic Formation of a Cyclic Siloxane Intermediate |
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| Authors: | M. Sc. Nikolaos Drosos Dr. Bill Morandi |
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| Affiliation: | Max‐Planck‐Institut für Kohlenforschung, Kaiser‐Wilhelm‐Platz 1, 45470 Mülheim an der Ruhr (Germany) |
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| Abstract: | The selective deoxygenation of polyols is a frontier in our ability to harness the stereochemical and structural complexity of natural and synthetic feedstocks. Herein, we describe a highly active and selective boron‐based catalytic system for the selective deoxygenation of terminal 1,2‐diols at the primary position, a process that is enabled by the transient formation of a cyclic siloxane. The method provides an ideal complement to well‐known catalytic asymmetric reactions to prepare synthetically challenging chiral 2‐alkanols in nearly perfect enantiomeric excess, as illustrated in a short synthesis of the anti‐inflammatory drug (R)‐lisofylline. |
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| Keywords: | boron cyclic intermediates deoxygenation diols silanes |
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