Synthesis of (R)-propane-1,2-diol from lactides by dynamic kinetic resolution |
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Authors: | Ivan A Shuklov Natalia V Dubrovina Joachim Schulze Wolfgang Tietz Armin Börner |
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Institution: | 1. Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert-Einstein Straße 29a, 18059 Rostock, Germany;2. ThyssenKrupp Industrial Solutions GmbH, Am Haupttor, Bau 3668, 06237 Leuna, Germany;3. Institut für Chemie der Universität Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany |
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Abstract: | The dynamic kinetic resolution (DKR) of rac-1-tert-butoxypropan-2-ol with isopropenyl acetate in the presence of Novozyme 435 and a ruthenium catalyst produces enantiomerically pure (R)-1-tert-butoxy-2-acetoxy-propane (>99.5 %ee) in a good yield. The product can be easily transformed into (R)-propane-1,2-diol without loss of stereoselectivity. Together with recently published procedures, the herein described DKR offers the possibility to use any lactide source as starting material for the production of (R)-propane-1,2-diol. The chiral diol may serve as the chiral building block for the synthesis of important enantiopure esters, like propylene carbonate, chiral polymers, etc. |
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Keywords: | Propane-1 2-diol Lactide Dynamic kinetic resolution Ruthenium PLLA Lipase |
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