N‐Heterocyclic Carbene‐Catalyzed Double Michael Addition: Stereoselective Synthesis of Spirofluorenes and Multisubstituted Indanes

The strong Brønsted 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 yi...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-04, Vol.360 (8), p.1704-1710
Main Authors: Xing, Fen, Feng, Ze‐Nan, Wang, Ying, Du, Guang‐Fen, Gu, Cheng‐Zhi, Dai, Bin, He, Lin
Format: Article
Language:English
Subjects:
Brønsted base
Carbenes
Chemical synthesis
double Michael addition
Ketones
N-heterocyclic carbene
spirofluorene, indane
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Summary:The strong Brønsted 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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701269