Bidentate Lewis Acid Catalyzed Domino Diels–Alder Reaction of Phthalazine for the Synthesis of Bridged Oligocyclic Tetrahydronaphthalenes

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• 作者：Luca Schweighauser ; Ina Bodoky ; Simon N. Kessler ; Daniel Häussinger ; Carsten Donsbach ; Hermann A. Wegner
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 18, 2016
• 年：2016
• 卷：18
• 期：6
• 页码：1330-1333
• 全文大小：286K
• ISSN：1523-7052

文摘

A domino process consisting of an inverse and a normal electron-demand Diels–Alder reaction is presented for the formation of bridged tri- and tetracyclic 1,2,3,4-tetrahydronaphthalenes catalyzed by a bidentate Lewis acid. The products were synthesized in a one-pot reaction from commercially available starting materials and contain up to six stereogenic centers. The tetrahydronaphthalenes were isolated as single diastereomers and are derivatives of phenylethylamine, which is well-known as a scaffold of amphetamine or dopamine.