Towards Sustainable Amino Acid Derived Organocatalysts for Asymmetric syn‐Aldol Reactions

The undesirable side‐processes responsible for the fast deactivation of primary amino acid derived organocatalysts in asymmetric aldol reactions are identified. A new ionic‐liquid‐supported (S)‐valine‐/(S)‐α,α‐diphenylserinol‐derived catalyst (9) is designed on the basis of these results and exhibit...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-05, Vol.2017 (17), p.2540-2544
Main Authors: Gerasimchuk, Vasiliy V., Kucherenko, Alexandr S., Fakhrutdinov, Artem N., Medvedev, Michael G., Nelyubina, Yulia V., Zlotin, Sergei G.
Format: Article
Language:English
Subjects:
Aldehydes
Aldol reactions
Amino acids
Asymmetric synthesis
Asymmetry
Cascade chemical reactions
Catalysts
Chemical synthesis
Ionic liquids
Organocatalysis
Recyclability
Stereoselectivity
Valine
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Summary:The undesirable side‐processes responsible for the fast deactivation of primary amino acid derived organocatalysts in asymmetric aldol reactions are identified. A new ionic‐liquid‐supported (S)‐valine‐/(S)‐α,α‐diphenylserinol‐derived catalyst (9) is designed on the basis of these results and exhibits much better recyclability in asymmetric syn‐aldol reactions between hydroxyacetone and aldehydes. Furthermore, this catalyst appeared to be useful for the stereoselective synthesis of the naturally occurring 1(3H)‐isobenzofuran‐1‐one scaffold through an asymmetric syn‐aldol/lactonization cascade reaction. The undesirable side‐processes responsible for the fast deactivation of primary amino acid derived organocatalysts are identified. An ionic‐liquid‐supported (S)‐valine‐/(S)‐α,α‐diphenylserinol‐derived catalyst is designed on the basis of these results and exhibits promising sustainability in asymmetric syn‐aldol reactions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700166