Sustainable domino Michael reaction catalyzed by a Brønsted base on silica gel: synthesis of bicyclo[2.2.2]octane-2,5-dione derivatives |
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| Authors: | Masakazu Fukushima Takashi Hoshi Hisahiro Hagiwara |
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| Affiliation: | a Graduate School of Science and Technology, Niigata University, 8050, 2-Nocho, Ikarashi, Niigata 950-2181, Japan
b Faculty of Engineering, Niigata University, 8050, 2-Nocho, Ikarashi, Niigata 950-2181, Japan |
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| Abstract: | Domino Michael reactions of oxophorone and its derivatives 4 with Michael partners 3 have been effected to give bicyclo[2.2.2]octane-2,5-dione derivatives 7 by a catalytic amount of a Brønsted base (NMAP-Li) generated from N-methylaminopropylated silica gel (NMAP) and n-BuLi. The NMAP pellets were efficiently reused up to six times in 86% average yield. |
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| Keywords: | Domino reaction Michael reaction Silica gel anion Heterogeneous base |
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