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http://dx.doi.org/10.5012/bkcs.2004.25.4.491

Lewis Acid-Catalyzed Reactions of Anthrone: Preference for Cycloaddition Reaction over Conjugate Addition Depending on the Functionality of α,β-Unsaturated Carbonyl Compounds  

Baik, Woon-Phil (Department of Chemistry, Myoun Ji University)
Yoon, Cheol-Hoon (Department of Chemistry, Myoun Ji University)
Koo, Sang-Ho (Department of Chemistry, Myoun Ji University)
Kim, Ha-Kwon (Department of Chemistry and GNRL, Kyung Hee University)
Kim, Ji-Han (Department of Chemistry and GNRL, Kyung Hee University)
Kim, Jeong-Ryul (Department of Chemistry and GNRL, Kyung Hee University)
Hong, Soo-Dong (Department of Chemistry and GNRL, Kyung Hee University)
Publication Information
Bulletin of the Korean Chemical Society / v.25, no.4, 2004 , pp. 491-500 More about this Journal
Abstract
The Lewis acid-catalyzed reactions of anthrone with a variety of ethylenic substrates under various conditions have been studied. It has been observed that depending on kinds of ethylenic substrates and catalysts, products were varied. In particular, the $ZnCl_2$-catalyzed reaction of anthrone with ${\alpha},{\beta}$ -unsaturated ester gave bridged compounds 3 (Diels-Alder adduct type) and mono-Michael adduct 4 exclusively, while the base-catalyzed reaction gave 10,10-bis-Michael adduct as a major product independent of the amount of ethylenic substrate and base. Bridged compounds 3 were easily converted to the corresponding mono-Michael adduct 4 by a catalytic amount of base. Further Michael reaction of mono-Michael adducts with different ethylenic substrates in the presence of a catalytic amount of alkoxide gave unsymmetrical 10,10-bis Michael adducts in good or moderate yields.
Keywords
Anthrone; Lewis acid; Cycloaddition; Conjugated addition; Michael reaction;
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