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Asymmetric Lewis Acid Catalysis in Water: α‐Amino Acids as Effective Ligands in Aqueous Biphasic Catalytic Michael Additions
Author(s) -
Aplander Karolina,
Ding Rui,
Krasavin Mikhail,
Lindström U. Marcus,
Wennerberg Johan
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800922
Subject(s) - chemistry , lewis acids and bases , catalysis , ligand (biochemistry) , chiral lewis acid , amino acid , aqueous solution , enantiomer , lewis acid catalysis , michael reaction , yield (engineering) , organic chemistry , selectivity , enantioselective synthesis , combinatorial chemistry , medicinal chemistry , biochemistry , materials science , receptor , metallurgy
This article explores the potential of native α‐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 /α‐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 α‐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 α‐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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)