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Title: Correlation between Chiral Modifier Adsorption and Enantioselectivity in Hydrogenation Catalysis

Authors:
 [1];  [1];  [1]; ORCiD logo [1]
  1. Department of Chemistry and UCR Center for Catalysis, University of California, Riverside CA 92521 USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1378795
Grant/Contract Number:  
SC0008703
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Angewandte Chemie
Additional Journal Information:
Journal Name: Angewandte Chemie Journal Volume: 129 Journal Issue: 27; Journal ID: ISSN 0044-8249
Publisher:
German Chemical Society
Country of Publication:
Germany
Language:
English

Citation Formats

Ni, Yufei, Gordon, Alexander D., Tanicala, Florisa, and Zaera, Francisco. Correlation between Chiral Modifier Adsorption and Enantioselectivity in Hydrogenation Catalysis. Germany: N. p., 2017. Web. doi:10.1002/ange.201704880.
Ni, Yufei, Gordon, Alexander D., Tanicala, Florisa, & Zaera, Francisco. Correlation between Chiral Modifier Adsorption and Enantioselectivity in Hydrogenation Catalysis. Germany. https://doi.org/10.1002/ange.201704880
Ni, Yufei, Gordon, Alexander D., Tanicala, Florisa, and Zaera, Francisco. Mon . "Correlation between Chiral Modifier Adsorption and Enantioselectivity in Hydrogenation Catalysis". Germany. https://doi.org/10.1002/ange.201704880.
@article{osti_1378795,
title = {Correlation between Chiral Modifier Adsorption and Enantioselectivity in Hydrogenation Catalysis},
author = {Ni, Yufei and Gordon, Alexander D. and Tanicala, Florisa and Zaera, Francisco},
abstractNote = {},
doi = {10.1002/ange.201704880},
journal = {Angewandte Chemie},
number = 27,
volume = 129,
place = {Germany},
year = {Mon May 15 00:00:00 EDT 2017},
month = {Mon May 15 00:00:00 EDT 2017}
}

Works referenced in this record:

Cinchona-Modified Platinum Catalysts: From Ligand Acceleration to Technical Processes
journal, December 2007

  • Blaser, Hans-Ulrich; Studer, Martin
  • Accounts of Chemical Research, Vol. 40, Issue 12
  • DOI: 10.1021/ar700088f

Origins of Enantioselectivity in Reductions of Ketones on Cinchona Alkaloid Modified Platinum
journal, January 2004

  • Vayner, Grigoriy; Houk, K. N.; Sun, Y. -K.
  • Journal of the American Chemical Society, Vol. 126, Issue 1
  • DOI: 10.1021/ja035147f

Dependence of the adsorption of chiral compounds on their enantiomeric composition
journal, November 2014


Factors Controlling Adsorption Equilibria from Solution onto Solid Surfaces:  The Uptake of Cinchona Alkaloids on Platinum Surfaces
journal, December 2007

  • Ma, Zhen; Lee, Ilkeun; Zaera, Francisco
  • Journal of the American Chemical Society, Vol. 129, Issue 51
  • DOI: 10.1021/ja076011a

Origin of enhanced rate in the platinum-catalysed enantioselective hydrogenation of methyl pyruvate
journal, September 1991


The Role of Modifier Structure in Heterogeneous Enantioselective Hydrogenation:  One-to-One Interactions of 1-Phenyl-1,2-propanedione and Methyl Pyruvate with Modifiers on the Pt(111) Surface
journal, March 2007

  • Taskinen, Antti; Nieminen, Ville; Hotokka, Matti
  • The Journal of Physical Chemistry C, Vol. 111, Issue 13, 5128-5140
  • DOI: 10.1021/jp067017

Enantioselective Hydrogenation of Ethyl Pyruvate over Pt/Alumina Modified by (R)-1-(1-Naphthyl)ethylamine Derivatives
journal, May 1996


Probing Liquid/Solid Interfaces at the Molecular Level
journal, January 2012


Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS
journal, January 2006

  • Kraynov, A.; Suchopar, A.; D’Souza, L.
  • Physical Chemistry Chemical Physics, Vol. 8, Issue 11
  • DOI: 10.1039/b514750f

Direct Observation of Molecular Preorganization for Chirality Transfer on a Catalyst Surface
journal, November 2011


Adsorption and stability of chiral modifiers based on 1-(1-naphthyl)-ethylamine for Pt catalysed heterogeneous asymmetric hydrogenations
journal, January 2015

  • Meemken, Fabian; Steiger, Titian; Holland, Mareike C.
  • Catalysis Science & Technology, Vol. 5, Issue 2
  • DOI: 10.1039/C4CY01136H

Unexpected Inversion in Enantioselectivity in the Hydrogenation N-acetyl Dehydrophenylalanine Methyl Ester using Cinchona-Modified Pd/Al2O3 catalyst
journal, September 2005

  • Colston, Nichola J.; Wells, Richard P. K.; Wells, Peter B.
  • Catalysis Letters, Vol. 103, Issue 1-2
  • DOI: 10.1007/s10562-005-6512-8

A decade+ of operando spectroscopy studies
journal, April 2017


1-(1-Naphthyl)Ethylamine Adsorption on Platinum Surfaces: On the Mechanism of Chiral Modification in Catalysis
journal, November 2008

  • Lee, Ilkeun; Ma, Zhen; Kaneko, Shinji
  • Journal of the American Chemical Society, Vol. 130, Issue 44
  • DOI: 10.1021/ja803667v

Adsorption and thermal decomposition of N-methylaniline on Pt(111)
journal, November 2009


Water at Interfaces
journal, April 2016


Adsorption of 1-(1-Naphthyl)ethylamine from Solution onto Platinum Surfaces: Implications for the Chiral Modification of Heterogeneous Catalysts
journal, February 2013

  • Gordon, Alexander D.; Zaera, Francisco
  • Angewandte Chemie International Edition, Vol. 52, Issue 12
  • DOI: 10.1002/anie.201209815

Role of the modifier in the enantioselective hydrogenation of ethyl pyruvate over Pt/Al2O3 catalyst
journal, January 1990

  • Margitfalvi, J. L.; Marti, P.; Baiker, A.
  • Catalysis Letters, Vol. 6, Issue 3-6
  • DOI: 10.1007/BF00763994

1-(1-Naphthyl)ethylamine and derivatives thereof as chiral modifiers in the enantioselective hydrogenation of ethyl pyruvate over Pt–alumina
journal, January 1995

  • Heinz, Thomas; Wang, Guozhi; Pfaltz, Andreas
  • J. Chem. Soc., Chem. Commun., Issue 14
  • DOI: 10.1039/C39950001421

Highly Enantioselective Heterogeneously Catalyzed Hydrogenation of α-Ketoesters under Mild Conditions
journal, May 1999

  • LeBlond, C.; Wang, J.; Liu, J.
  • Journal of the American Chemical Society, Vol. 121, Issue 20
  • DOI: 10.1021/ja990653j

Atomic-Scale Observations of Catalyst Structures under Reaction Conditions and during Catalysis
journal, March 2016

  • Tao, Franklin (Feng); Crozier, Peter A.
  • Chemical Reviews, Vol. 116, Issue 6
  • DOI: 10.1021/cr5002657

Enantioselective hydrogenation of ethyl pyruvate catalysed by cinchonine-modified Pt/Al2O3: tilted adsorption geometry of cinchonine
journal, April 2005

  • Bartók, Mihály; Sutyinszki, Mária; Balázsik, Katalin
  • Catalysis Letters, Vol. 100, Issue 3-4
  • DOI: 10.1007/s10562-004-3449-2

In Situ Characterization of Adsorbates in Solid−Liquid Interfaces by Reflection−Absorption Infrared Spectroscopy
journal, April 2003

  • Kubota, Jun; Ma, Zhen; Zaera, Francisco
  • Langmuir, Vol. 19, Issue 8
  • DOI: 10.1021/la027031n

Enantioselective hydrogenation of ethyl pyruvate over Pt/alumina: systematic variation of the modifier structure
journal, December 1997