Asymmetric Aminocatalysis in the Synthesis of δ‐Lactone Derivatives | Zendy

Albrecht Anna | Zendy; Skrzyńska Anna | Zendy; Pietrzak Anna | Zendy; Bojanowski Jan | Zendy; Albrecht Łukasz | Zendy

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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.

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