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N-Heterocyclic Carbene-Catalyzed Double Michael Addition: Stereoselective Synthesis of Spirofluorenes and Multisubstituted Indanes
The strong Br¡ãnsted basic character of N-heterocyclic carbenes (NHCs) has been used to promote the cascade double Michael addition between fluorenes and dienones. Under catalyst loadings of 1?5 mol% of NHC, fluorene reacts with divinyl ketones (DVKs) to afford anti-spirofluorene compounds in high yields. However, when benzenedi(enones) were employed as Michael acceptors in the presence of 10 mol% of NHC, fluorene undergoes a different inter- and intramolecular cascade double Michael addition, providing multi-substituted indanes in high yields with excellent diastereoselectivity. (Figure presented.).
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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate