Unexpected change of the sense of the enantioselective hydrogenation of ethyl pyruvate catalyzed by a Pt-alumina-cinchona alkaloid system

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Abstract

In the enantioselective hydrogenation of ethyl pyruvate (EtPy) over β-isocinchonine (β-ICN) modified Pt-alumina catalysts, the major enantiomer was (R)-ethyl lactate ((R)-EtLt (ee 50%)) in toluene, while in AcOH (S)-EtLt (ee 60%) was formed; the (R) configuration is opposite to what is expected from the absolute configuration of the cinchonine backbone.

Original languageEnglish
Pages (from-to)1130-1131
Number of pages2
JournalChemical Communications
Issue number10
Publication statusPublished - May 23 2002

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Cinchona Alkaloids
Enantiomers
Aluminum Oxide
Toluene
Hydrogenation
Alumina
Catalysts
ethyl pyruvate
cinchonine
ethyl lactate

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "In the enantioselective hydrogenation of ethyl pyruvate (EtPy) over β-isocinchonine (β-ICN) modified Pt-alumina catalysts, the major enantiomer was (R)-ethyl lactate ((R)-EtLt (ee 50{\%})) in toluene, while in AcOH (S)-EtLt (ee 60{\%}) was formed; the (R) configuration is opposite to what is expected from the absolute configuration of the cinchonine backbone.",
author = "M. Bart{\'o}k and M. Sutyinszki and K. Felf{\"o}ldi and G. Sz{\"o}llősi",
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AU - Bartók, M.

AU - Sutyinszki, M.

AU - Felföldi, K.

AU - Szöllősi, G.

PY - 2002/5/23

Y1 - 2002/5/23

N2 - In the enantioselective hydrogenation of ethyl pyruvate (EtPy) over β-isocinchonine (β-ICN) modified Pt-alumina catalysts, the major enantiomer was (R)-ethyl lactate ((R)-EtLt (ee 50%)) in toluene, while in AcOH (S)-EtLt (ee 60%) was formed; the (R) configuration is opposite to what is expected from the absolute configuration of the cinchonine backbone.

AB - In the enantioselective hydrogenation of ethyl pyruvate (EtPy) over β-isocinchonine (β-ICN) modified Pt-alumina catalysts, the major enantiomer was (R)-ethyl lactate ((R)-EtLt (ee 50%)) in toluene, while in AcOH (S)-EtLt (ee 60%) was formed; the (R) configuration is opposite to what is expected from the absolute configuration of the cinchonine backbone.

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