Synthesis of 4-Vinyl-1,2,3,4-tetrahydroisoquinoline from N-Tethered Benzyl-Alkenol Catalyzed by Indium(III) Chloride: Formal Synthesis of (±)-Isocyclocelabenzine,Synthesis

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Synthesis of 4-Vinyl-1,2,3,4-tetrahydroisoquinoline from N-Tethered Benzyl-Alkenol Catalyzed by Indium(III) Chloride: Formal Synthesis of (±)-Isocyclocelabenzine
Synthesis ( IF 2.2 ) Pub Date : 2020-02-12 , DOI: 10.1055/s-0037-1610750
Anil K. Saikia ₁ , Ngangbam Renubala Devi , Sudip Shit , Bipin Kumar Behera

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An intramolecular Friedel–Crafts cyclization reaction catalyzed by indium(III) chloride for the formation of 4-vinyl-1,2,3,4-tetrahydroisoquinoline from N-tethered benzyl-alkenol in good yields has been described. The reaction is highly regioselective and generates an exocyclic vinyl functionality in the piperidine ring. The reaction is compatible with a wide range of functional groups. The strategy is demonstrated for the formal synthesis of (±)-isocyclocelabenzine alkaloid.

中文翻译：

氯化铟（III）催化的N系苄基链烯醇的合成4-乙烯基-1,2,3,4-四氢异喹啉：（±）-异环celabenzine的形式合成

已经描述了用氯化铟（III）催化的分子内Friedel-Crafts环化反应，以高收率由N-束缚的苄基烯醇形成4-乙烯基-1,2,3,4-四氢异喹啉。该反应是高度区域选择性的，并在哌啶环中产生环外乙烯基官能团。该反应与多种官能团相容。证明了该策略用于（±）-异环菜烯碱生物碱的正式合成。

更新日期：2020-02-13

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