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Issue 3, 2005
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Combined epimerisation and acylation: Meerwein–Ponndorf–Verley–Oppenauer catalysts in action

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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.

Graphical abstract: Combined epimerisation and acylation: Meerwein–Ponndorf–Verley–Oppenauer catalysts in action

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Publication details

The article was received on 10 Sep 2004, accepted on 16 Nov 2004 and first published on 17 Dec 2004


Article type: Paper
DOI: 10.1039/B413944E
Citation: Org. Biomol. Chem., 2005,3, 483-489
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    Combined epimerisation and acylation: Meerwein–Ponndorf–Verley–Oppenauer catalysts in action

    D. Klomp, K. Djanashvili, N. C. Svennum, N. Chantapariyavat, C. Wong, F. Vilela, T. Maschmeyer, J. A. Peters and U. Hanefeld, Org. Biomol. Chem., 2005, 3, 483
    DOI: 10.1039/B413944E

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