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Asymmetric Lewis Acid Catalysis in Water: alpha-Amino Acids as Effective Ligands in Aqueous Biphasic Catalytic Michael Additions

Aplander, Karolina LU ; Ding, Rui LU ; Krasavin, Mikhail; Lindstrom, U. Marcus and Wennerberg, Johan (2009) In European Journal of Organic Chemistry p.810-821
Abstract
This article explores the potential of native a-amino acids as chiral ligands in aqueous asymmetric Lewis acid catalysis, employing the C-C bond forming Michael addition as a model reaction. Some insights are provided regarding the details of Yb(OTf)(3)/alpha-amino acid-catalyzed Michael additions in water through new kinetic data as well as studies on how both yield and selectivity are influenced by variations in metal/ligand ratio, pH, temperature, and structure of the a-amino acid, Through this investigation it was found that reaction conditions that require only 5 mol-% of the Lewis acid, provides enantiomeric excesses of up to 79 % and is applicable to a wider range of donors and acceptors than previously demonstrated. Importantly, it... (More)
This article explores the potential of native a-amino acids as chiral ligands in aqueous asymmetric Lewis acid catalysis, employing the C-C bond forming Michael addition as a model reaction. Some insights are provided regarding the details of Yb(OTf)(3)/alpha-amino acid-catalyzed Michael additions in water through new kinetic data as well as studies on how both yield and selectivity are influenced by variations in metal/ligand ratio, pH, temperature, and structure of the a-amino acid, Through this investigation it was found that reaction conditions that require only 5 mol-% of the Lewis acid, provides enantiomeric excesses of up to 79 % and is applicable to a wider range of donors and acceptors than previously demonstrated. Importantly, it was also demonstrated that the a-amino acid complexed ytterbium. catalyst might have potential for large-scale applications as it displays not only large ligand accelerations, but also good solubility and stability in water. It can be recycled multiple times without appreciable loss of activity. The result is a promising example of a water-compatible chiral Lewis acid. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Homogeneous catalysis, Asymmetric catalysis, Water-tolerant Lewis, acids, Michael addition, Recyclable catalyst, Amino acids, Reaction mechanisms
in
European Journal of Organic Chemistry
issue
6
pages
810 - 821
publisher
John Wiley & Sons
external identifiers
  • wos:000263648200006
  • scopus:60849139404
ISSN
1434-193X
DOI
10.1002/ejoc.200800922
language
English
LU publication?
yes
id
2d9e7f80-24b0-462c-bc43-f08c89ef0dda (old id 1371865)
date added to LUP
2009-05-07 14:41:52
date last changed
2017-11-05 03:39:50
@article{2d9e7f80-24b0-462c-bc43-f08c89ef0dda,
  abstract     = {This article explores the potential of native a-amino acids as chiral ligands in aqueous asymmetric Lewis acid catalysis, employing the C-C bond forming Michael addition as a model reaction. Some insights are provided regarding the details of Yb(OTf)(3)/alpha-amino acid-catalyzed Michael additions in water through new kinetic data as well as studies on how both yield and selectivity are influenced by variations in metal/ligand ratio, pH, temperature, and structure of the a-amino acid, Through this investigation it was found that reaction conditions that require only 5 mol-% of the Lewis acid, provides enantiomeric excesses of up to 79 % and is applicable to a wider range of donors and acceptors than previously demonstrated. Importantly, it was also demonstrated that the a-amino acid complexed ytterbium. catalyst might have potential for large-scale applications as it displays not only large ligand accelerations, but also good solubility and stability in water. It can be recycled multiple times without appreciable loss of activity. The result is a promising example of a water-compatible chiral Lewis acid. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)},
  author       = {Aplander, Karolina and Ding, Rui and Krasavin, Mikhail and Lindstrom, U. Marcus and Wennerberg, Johan},
  issn         = {1434-193X},
  keyword      = {Homogeneous catalysis,Asymmetric catalysis,Water-tolerant Lewis,acids,Michael addition,Recyclable catalyst,Amino acids,Reaction mechanisms},
  language     = {eng},
  number       = {6},
  pages        = {810--821},
  publisher    = {John Wiley & Sons},
  series       = {European Journal of Organic Chemistry},
  title        = {Asymmetric Lewis Acid Catalysis in Water: alpha-Amino Acids as Effective Ligands in Aqueous Biphasic Catalytic Michael Additions},
  url          = {http://dx.doi.org/10.1002/ejoc.200800922},
  year         = {2009},
}