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

Bulletin of the Korean chemical society

Hakwon Kim¹  Woonphil Baik¹  Soodong Hong¹  Jihan Kim¹  Cheol Hoon Yoon¹  Jeongryul Kim¹  Sangho Koo¹ 

关键词: Anthrone;    Lewis acid;    Cycloaddition;    Conjugated addition;    Michael reaction;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

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 ZnCl₂-catalyzed reaction of anthrone with �?, �?-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.

【 授权许可】

Unknown