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Towards Sustainable Amino Acid Derived Organocatalysts for Asymmetric syn ‐Aldol Reactions
Author(s) -
Gerasimchuk Vasiliy V.,
Kucherenko Alexandr S.,
Fakhrutdinov Artem N.,
Medvedev Michael G.,
Nelyubina Yulia V.,
Zlotin Sergei G.
Publication year - 2017
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.201700166
Subject(s) - aldol reaction , chemistry , organocatalysis , stereoselectivity , catalysis , enantioselective synthesis , valine , organic chemistry , lewis acid catalysis , isobenzofuran , aldol condensation , amino acid , combinatorial chemistry , lewis acids and bases , biochemistry
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.