Lewis Acid Catalyzed Cascade Reaction of 3-(2-Benzenesulfonamide)propargylic Alcohols to Spiro[indene-benzosultam]s

Sun, Lang; Zhu, Yuanxun; Wang, Jing; Lu, Ping; Wang, Yanguang

Lewis Acid Catalyzed Cascade Reaction of 3-(2-Benzenesulfonamide)propargylic Alcohols to Spiro[indene-benzosultam]s

2015

Sun, Lang | Zhu, Yuanxun | Wang, Jing | Lu, Ping | Wang, Yanguang

A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel–Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.

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