Dynamic Kinetic Resolution over Cinchona-Modified Platinum Catalyst: Hydrogenation of Racemic Ethyl 2-Fluoroacetoacetate

The enantioselective hydrogenation over a Cinchona alkaloid‐modified supported platinum catalyst and parallel spontaneous racemization under the reaction conditions of the unreacted enantiomer of ethyl 2‐fluoroacetoacetate are described. Using the appropriate reaction conditions an 82% enantiomeric...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2006-03, Vol.348 (4-5), p.515-522
Main Authors: Szőri, Kornél, Szöllősi, György, Bartók, Mihály
Format: Article
Language:English
Subjects:
Cinchona alkaloids
dynamic kinetic resolution
enantioselectivity
heterogeneous catalysis
hydrogenation
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Summary:The enantioselective hydrogenation over a Cinchona alkaloid‐modified supported platinum catalyst and parallel spontaneous racemization under the reaction conditions of the unreacted enantiomer of ethyl 2‐fluoroacetoacetate are described. Using the appropriate reaction conditions an 82% enantiomeric excess in favor of the (2S,3R)‐ethyl 2‐fluoro‐3‐hydroxybutanoate and a 99/1 threo/erythro ratio were obtained. This novel method for producing optically enriched α‐fluoro‐β‐hydroxy esters is the first example of dynamic kinetic resolution of a chirally labile racemic fluorinated compound over a modified heterogeneous metal catalyst carried out without using supplementary additives except the chiral modifier. The hydrogenation described here shows that the activation of the keto group of acetoacetates by one fluorine atom in the α position is also sufficient for obtaining high enantiomeric excess in the Orito reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200505366