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Calcium‐Catalyzed Synthesis of Polysubstituted 2‐Alkenylfurans from β‐Keto Esters Tethered to Propargyl Alcohols
Author(s) -
Morcillo Sara P.,
Leboeuf David,
Bour Christophe,
Gandon Vincent
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603929
Subject(s) - propargyl , chemistry , catalysis , furan , tertiary alcohols , organic chemistry , calcium , reaction conditions , combinatorial chemistry
An efficient synthesis of polysubstituted 2‐alkenylfurans using Ca(NTf 2 ) 2 /KPF 6 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.