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Combined Epimerisation and Acylation: Meerwein-Ponndorf-Verley-Oppenauer Catalysts in Action

Combined Epimerisation and Acylation: Meerwein-Ponndorf-Verley-Oppenauer Catalysts in Action

Dirk Klomp, Kristina Djanashvili, Nina Cianfanelli Svennum, Nuttanun Chantapariyavat, Chung-Sing Wong, Filipe Vilela, Thomas Maschmeyer, Joop A Peters, Ulf Hanefeld

Org Biomol Chem. 2005 Feb 7;3(3):483-9.

PMID: 15678186

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP19236158	Neodymium(III) isopropoxide		19236-15-8	Price

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