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Cascade Olefin Isomerization/Intramolecular Diels–Alder Reaction Catalyzed by N‐Heterocyclic Carbenes
Author(s) -
Kowalczyk Marcin,
Lupton David W.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402067
Subject(s) - isomerization , intramolecular force , olefin fiber , catalysis , chemistry , diels–alder reaction , cascade , cascade reaction , organic chemistry , photochemistry , chromatography
The addition of an N‐heterocyclic carbene to the carbonyl group of an α,β,γ,δ‐unsaturated enol ester affords a hemiacetal azolium intermediate that enables a cascade olefin isomerization/Diels–Alder reaction, for which mechanistic studies implicate Lewis base catalysis. Preliminary studies into the utility of the products have been undertaken with reductive and oxidative cleavage, giving materials for potential use in complex‐target synthesis.