Combined epimerisation and acylation: Meerwein-Ponndorf-Verley-Oppenauer catalysts in action |
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Authors: | Klomp Dirk Djanashvili Kristina Svennum Nina Cianfanelli Chantapariyavat Nuttanun Wong Chung-Sing Vilela Filipe Maschmeyer Thomas Peters Joop A Hanefeld Ulf |
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Affiliation: | Gebouw voor Scheikunde, Delft University of Technology, Julianalaan 136, 2628 BL Delft, The Netherlands. |
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Abstract: | A practical racemisation-epimerisation method for chiral secondary alcohols has been developed. Meerwein-Ponndorf-Verley-Oppenauer catalysts such as neodymium(III) isopropoxide are able to racemise these alcohols with retention of other stereocentres in the molecule. This is particularly useful for the recycling of the undesired products of kinetic resolutions of alcohols. By combination of such a racemisation with an acylation using isopropenyl or ethoxyvinyl esters as acyl donors, a fast straightforward recycling of starting materials may be achieved. The combined epimerisation and acylation process is demonstrated for the steroid estradiol methyl ether. |
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