Calcium-Catalyzed Synthesis of Polysubstituted 2-Alkenylfurans from β-Keto Esters Tethered to Propargyl Alcohols

An efficient synthesis of polysubstituted 2‐alkenylfurans using Ca(NTf2)2/KPF6 as a catalytic mixture is described. It is based on the cycloelimination of readily available propargyl alcohols tethered to β‐keto esters under dry conditions to avoid competitive Meyer–Schuster rearrangement. The furan...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-11, Vol.22 (47), p.16974-16978
Main Authors: Morcillo, Sara P., Leboeuf, David, Bour, Christophe, Gandon, Vincent
Format: Article
Language:English
Subjects:
alcohol
Biocompatibility
calcium
carbocation
Catalysis
Catalysts
cyclization
Drying
Esters
furan
Furans
Propargyl alcohol
Synthesis (chemistry)
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Summary:An efficient synthesis of polysubstituted 2‐alkenylfurans using Ca(NTf2)2/KPF6 as a catalytic mixture is described. It is based on the cycloelimination of readily available propargyl alcohols tethered to β‐keto esters under dry conditions to avoid competitive Meyer–Schuster rearrangement. The furan can be further functionalized in situ by a calcium‐catalyzed Friedel–Crafts‐type reaction with secondary and tertiary alcohols. The title reaction allows for the high‐yielding preparation of di‐, tri‐, and tetrasubstituted 2‐alkenylfurans, which are important subunits of bioactive compounds. An efficient synthesis of polysubstituted 2‐alkenylfurans using Ca(NTf2)2/KPF6 as the catalytic mixture is described. The reaction allows for the high‐yielding preparation of di‐, tri‐, and tetrasubstituted 2‐alkenylfurans, which are important subunits of bioactive compounds.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201603929