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Base‐Catalyzed Tandem Michael/Dehydro‐Diels–Alder Reaction of α,α‐Dicyanoolefins with Electron‐Deficient 1,3‐Conjugated Enynes: A Facile Entry to Angularly Fused Polycycles
Author(s) -
Zhang Mingrui,
Zhang Junliang
Publication year - 2014
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.201302960
Subject(s) - olefin fiber , conjugated system , cycloaddition , tandem , chemistry , heteroatom , catalysis , michael reaction , combinatorial chemistry , base (topology) , cascade reaction , dabco , organic chemistry , ring (chemistry) , materials science , polymer , mathematics , composite material , mathematical analysis
Angularly fused carbocyclic frameworks and their heteroatom‐substituted analogues exist in many natural products that display a broad and interesting range of biological activities. Preparation of polycyclic products by cycloaddition reactions have been the long‐standing hot topic in the synthetic community. Dehydro‐Diels–Alder (DDA) reactions are one class of dehydropericyclic reactions that are derived conceptually by systematic removal of hydrogen atom pairs. A base‐promoted tandem Michael addition and DDA reaction of α,α‐dicyanoolefins with electron‐deficient 1,3‐conjugated enynes was realized in which a DDA reaction takes place between the arylalkynes and electron‐deficient tetrasubstituted olefin. The control experiments support the stepwise anionic reaction pathway rather than the concerted reaction pathway.