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

doi:10.1007/s10562-006-0096-9

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	135-138
Number of pages	4
Journal	Catalysis Letters
Volume	110
Issue number	1-2
DOIs	https://doi.org/10.1007/s10562-006-0096-9
Publication status	Published - Aug 2006

Bibliographical note

We thank the Leverhulme Trust, the Commonwealth of Pennsylvania and King Abdul Aziz University (Saudi Arabia Government) for financial support.

Keywords

enantioselective hydrogenation
enantio-inversion
ethyl pyruvate hydrogenation

Access to Document

10.1007/s10562-006-0096-9Licence: Unspecified

Cite this

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

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.",

keywords = "enantioselective hydrogenation, enantio-inversion, ethyl pyruvate hydrogenation",

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

note = "We thank the Leverhulme Trust, the Commonwealth of Pennsylvania and King Abdul Aziz University (Saudi Arabia Government) for financial support.",

year = "2006",

month = aug,

doi = "10.1007/s10562-006-0096-9",

language = "English",

volume = "110",

pages = "135--138",

journal = "Catalysis Letters",

issn = "1011-372X",

publisher = "Springer Netherlands",

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TY - JOUR

T1 - Unexpected inversion of enantioselectivity during the hydrogenation of ethyl pyruvate using hydroquinine and hydroquinidine modified Pt/Al2O3

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.

N1 - We thank the Leverhulme Trust, the Commonwealth of Pennsylvania and King Abdul Aziz University (Saudi Arabia Government) for financial support.

PY - 2006/8

Y1 - 2006/8

N2 - 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.

AB - 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.

KW - enantioselective hydrogenation

KW - enantio-inversion

KW - ethyl pyruvate hydrogenation

U2 - 10.1007/s10562-006-0096-9

DO - 10.1007/s10562-006-0096-9

M3 - Article

SN - 1011-372X

VL - 110

SP - 135

EP - 138

JO - Catalysis Letters

JF - Catalysis Letters

IS - 1-2

ER -