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Dearomatizative and Decarboxylative Reaction Cascade in the Aminocatalytic Synthesis of 3,4‐Dihydrocoumarins
Author(s) -
Bojanowski Jan,
Skrzyńska Anna,
Albrecht Anna
Publication year - 2019
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.201900222
Subject(s) - chemistry , furan , moiety , furfural , cascade , cascade reaction , coumarin , domino , alkyl , organic chemistry , cycloaddition , decarboxylation , deamination , combinatorial chemistry , catalysis , chromatography , enzyme
Within the performed study, a dearomatizative and decarboxylative reaction cascade for the synthesis of biologically relevant 3,4‐dihydrocoumarins has been developed. It utilizes 2‐alkyl‐3‐furfural derivatives that under aminocatalytic conditions are transformed into dienamine‐like intermediates in a process that involves dearomatization of the furan ring. Subsequent [4+2]‐cycloaddition with coumarin‐3‐carboxylic acids proceeds with rearomatization of the furan moiety. In the last step of the cascade, the aminocatalyst is released via decarboxylative deamination to give target 3,4‐dihydrocoumarins with excellent enantio‐ and diastereocontrol.