Lewis acid promoted dual bond formation: facile synthesis of dihydrocoumarins and spiro-tetracyclic dihydrocoumarins

Lewis acid (FeCl3) mediated dual bond (C-C and C-O) formation for synthesis of 3,4-dihydrocoumarins is presented. This method has successfully delivered a number of dihydrocoumarins containing dense functionalities on the aromatic ring. Significantly, the present method enabled achieving dihydrocoum...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-07, Vol.12 (25), p.4347-4360
Main Authors: Niharika, Pedireddi, Ramulu, Bokka Venkat, Satyanarayana, Gedu
Format: Article
Language:English
Subjects:
Chemistry, Organic - methods
Cinnamates - chemistry
Coumarins - chemical synthesis
Coumarins - chemistry
Cyclization
Lewis Acids - chemistry
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Stereoisomerism
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Summary:Lewis acid (FeCl3) mediated dual bond (C-C and C-O) formation for synthesis of 3,4-dihydrocoumarins is presented. This method has successfully delivered a number of dihydrocoumarins containing dense functionalities on the aromatic ring. Significantly, the present method enabled achieving dihydrocoumarins with tertiary as well as quaternary carbon atoms at the benzylic position. Gratifyingly, the novel spiro-tetracyclic lactones have also been dextrously prepared using this process.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00490f