The six-membered annulation reaction involving sequential palladium-catalyzed allylic alkylation and Michael addition: scope and limitations

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• 作者：Jousse-Karinthi ; Cé ; line ; Zouhiri ; Fatima ; Mahuteau ; Jacqueline ; Desma&euml ; le ; Didier
• 关键词：annulation ; sequential reaction ; Michael reaction ; palladium and compounds ; polycyclic aliphatic compounds
• 刊名：Tetrahedron
• 出版年：2003
• 出版时间：March 17, 2003
• 年：2003
• 卷：59
• 期：12
• 页码：2093-2099
• 全文大小：288 K

文摘

The palladium-catalyzed condensation of a variety of active methylene compounds with methyl 6-acetoxymethyl-hepta-2,6-dienoate was investigated. The six-membered adducts resulting from a η³ palladium complex alkylation–Michael addition sequence were obtained with moderate to good yields. In some cases, further evolution of the primary adduct was observed. The process has been expanded to access nitrogen heterocycles by using sodium p-toluenesulfonamide as the nucleophilic partner.