Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 8, Pages 1704-1710Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701269
Keywords
N-heterocyclic carbene; Bronsted base; double Michael addition; spirofluorene; indane
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Funding
- Excellent Young Teachers Plan of Bingtuan [CZ027203]
- Young Scientists Foundation of Shihezi University [RCZX201546, 2015ZRKXJQ05]
- National Natural Science Foundation of China [21662029]
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The strong Bronsted 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 1-5mol% 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 10mol% of NHC, fluorene undergoes a different inter- and intramolecular cascade double Michael addition, providing multi-substituted indanes in high yields with excellent diastereoselectivity.
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