Unexpected inversion of enantioselectivity during the hydrogenation of ethyl pyruvate using hydroquinine and hydroquinidine modified Pt/Al2O3

Robert L. Jenkins, Nicholas Dummer, Xiabao Li, Salem M. Bawaked, Paul McMorn, Richard P. K. Wells, Andrew Burrows, Christopher J. Kiely, Graham J. Hutchings

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

In the enantioselective hydrogenation of ethyl pyruvate using hydroquinidine 4-chlorobenzoate modified Pt/gamma-Al2O3 catalyst, the sense of the enantioselectivity is a function of the modifier concentration. At low concentration (S)-ethyl lactate is preferred and at higher concentration (R)-ethyl lactate is formed; the opposite trend is observed with hydroquinine 4-chlorobenzoate. This is the first example where enantio-inversion is induced solely as a function of the chiral modifier concentration.

Original languageEnglish
Pages (from-to)135-138
Number of pages4
JournalCatalysis Letters
Volume110
Issue number1-2
DOIs
Publication statusPublished - Aug 2006

Keywords

  • enantioselective hydrogenation
  • enantio-inversion
  • ethyl pyruvate hydrogenation

Cite this

Unexpected inversion of enantioselectivity during the hydrogenation of ethyl pyruvate using hydroquinine and hydroquinidine modified Pt/Al2O3. / Jenkins, Robert L.; Dummer, Nicholas; Li, Xiabao; Bawaked, Salem M.; McMorn, Paul; Wells, Richard P. K.; Burrows, Andrew; Kiely, Christopher J.; Hutchings, Graham J.

In: Catalysis Letters, Vol. 110, No. 1-2, 08.2006, p. 135-138.

Research output: Contribution to journalArticle

Jenkins, Robert L. ; Dummer, Nicholas ; Li, Xiabao ; Bawaked, Salem M. ; McMorn, Paul ; Wells, Richard P. K. ; Burrows, Andrew ; Kiely, Christopher J. ; Hutchings, Graham J. / Unexpected inversion of enantioselectivity during the hydrogenation of ethyl pyruvate using hydroquinine and hydroquinidine modified Pt/Al2O3. In: Catalysis Letters. 2006 ; Vol. 110, No. 1-2. pp. 135-138.
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abstract = "In the enantioselective hydrogenation of ethyl pyruvate using hydroquinidine 4-chlorobenzoate modified Pt/gamma-Al2O3 catalyst, the sense of the enantioselectivity is a function of the modifier concentration. At low concentration (S)-ethyl lactate is preferred and at higher concentration (R)-ethyl lactate is formed; the opposite trend is observed with hydroquinine 4-chlorobenzoate. This is the first example where enantio-inversion is induced solely as a function of the chiral modifier concentration.",
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AU - Jenkins, Robert L.

AU - Dummer, Nicholas

AU - Li, Xiabao

AU - Bawaked, Salem M.

AU - McMorn, Paul

AU - Wells, Richard P. K.

AU - Burrows, Andrew

AU - Kiely, Christopher J.

AU - Hutchings, Graham J.

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KW - enantioselective hydrogenation

KW - enantio-inversion

KW - ethyl pyruvate hydrogenation

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