4 years ago

Lewis Acid-Catalyzed [4+2] Annulation between Propargylic Alcohols with Benzo[d]isoxazoles

Lewis Acid-Catalyzed [4+2] Annulation between Propargylic Alcohols with Benzo[d]isoxazoles
Zhou Sun, Yong-Min Liang, Xian-Rong Song, Ming Li, Xue-Song Li, Ya-Ping Han, Xin-Yu Zhu
An unprecedented copper(II) trifluoromethanesulfonate-catalyzed [4+2] cascade annulation of propargylic alcohols with benzo[d]isoxazoles proceeds through a sequential ring opening/Meyer–Schuster rearrangement/intermolecular cyclization. This protocol, which tolerates a broad variety of functional groups, offers a versatile, modular and atom-economical access to a new class of fascinating quinoline derivatives in good yields under mild conditions. The transformation could be scaled up to a gram scale efficiently, thus highlighting the synthetic utility of this methodology.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700495

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