TY - JOUR
T1 - Combined epimerisation and acylation
T2 - Meerwein-ponndorf-verley-oppenauer catalysts in action
AU - Klomp, Dirk
AU - Djanashvili, Kristina
AU - Svennum, Nina Cianfanelli
AU - Chantapariyavat, Nuttanun
AU - Wong, Chung Sing
AU - Vilela, Filipe
AU - Maschmeyer, Thomas
AU - Peters, Joop A.
AU - Hanefeld, Ulf
PY - 2005
Y1 - 2005
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=14244250195&partnerID=8YFLogxK
U2 - 10.1039/b413944e
DO - 10.1039/b413944e
M3 - Article
AN - SCOPUS:14244250195
SN - 1477-0520
VL - 3
SP - 483
EP - 489
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 3
ER -