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Sustainable domino Michael reaction catalyzed by a Brønsted base on silica gel: synthesis of bicyclo[2.2.2]octane-2,5-dione derivatives

2005; Elsevier BV; Volume: 46; Issue: 19 Linguagem: Inglês

10.1016/j.tetlet.2005.03.092

1873-3581

Masakazu Fukushima, Satoru Endou, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara,

Catalytic Cross-Coupling Reactions

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.