A [3 + 2]-annulation approach to tetrasubstituted furans from MBH-carbonates of acetylenic aldehydes via sequential substitution/cycloisomerization

A novel metal-free approach to construct the tetrasubstituted furans from Morita-Baylis-Hillman (MBH)-carbonates of acetylenic aldehydes has been developed. This strategy involves the cascade nucleophilic substitution/5-exo-dig-cycloisomerization of MBH-carbonates with 1,3-dicarbonyl compounds to gi...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2015-08, Vol.13 (30), p.8310-8321
Main Authors: Reddy, Chada Raji, Mohammed, Siddique Z, Kumaraswamy, Paridala
Format: Article
Language:English
Subjects:
Acetylene - chemistry
Aldehydes - chemistry
Carbonates - chemistry
Chemistry, Organic - methods
Cyclization
Furans - chemical synthesis
Furans - chemistry
Isomerism
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Summary:A novel metal-free approach to construct the tetrasubstituted furans from Morita-Baylis-Hillman (MBH)-carbonates of acetylenic aldehydes has been developed. This strategy involves the cascade nucleophilic substitution/5-exo-dig-cycloisomerization of MBH-carbonates with 1,3-dicarbonyl compounds to give uniquely substituted 2-furan-3-yl acrylates. Additionally, the obtained furan adducts open a new entry to naphthofurans through palladium-catalyzed decarboxylative benzannulation.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00989h