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Asymmetric Aminocatalysis in the Synthesis of δ‐Lactone Derivatives
Author(s) -
Albrecht Anna,
Skrzyńska Anna,
Pietrzak Anna,
Bojanowski Jan,
Albrecht Łukasz
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600272
Subject(s) - chemistry , squaramide , bifunctional , moiety , cycloaddition , hydrogen bond , catalysis , structural motif , lactone , organocatalysis , stereochemistry , enantioselective synthesis , hydrogen , combinatorial chemistry , medicinal chemistry , organic chemistry , molecule , biochemistry
In this manuscript, a novel approach to 3,4‐dihydrocoumarins is presented. It utilizes the aminocatalytic, trienamine‐mediated cycloaddition reaction between 2,4‐dienals and ethyl coumarincarboxylates. The reaction is promoted by a bifunctional aminocatalyst bearing a hydrogen‐bonding squaramide structural unit. As a consequence, the stereochemical outcome is governed through the double hydrogen‐bonding interactions between the hydrogen‐bonding moiety of the catalyst and the dienophile. The transformation of the obtained cycloadducts into 3,4‐dihydrocoumarins bearing a bislactone structural motif is presented.