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 |
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| Authors: | Mingrui Zhang Prof. Junliang Zhang |
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| Affiliation: | 1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes. Department of Chemistry, East China Normal University, Shanghai 200062 (P. R. China);2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032 (P. R. China) |
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| Abstract: | 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. |
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| Keywords: | Diels– Alder reactions domino reactions enynes Michael reactions polycycles |
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