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Phosphine-catalyzed dearomative [3+2] cycloaddition of 4-nitroisoxazoles with allenoates or Morita-Baylis-Hillman carbonates.

Yongjun HeTian-Juan HeXiufang ChengYibo WeiHuamin WangYing-Wu Lin
Published in: Chemical communications (Cambridge, England) (2024)
An efficient phosphine-catalyzed dearomative [3+2] annulation of 4-nitroisoxazoles with allenoates or Morita-Baylis-Hillman carbonates has been established for the convenient synthesis of bicyclic isoxazoline derivatives. This reaction approach showed a broad substrate scope, high functional group compatibility, and excellent regioselectivity and diastereoselectivity. Furthermore, the success at the gram-scale and synthetic applications of the obtained compound 3a demonstrate the great potential of this methodology for practical applications in organic synthesis.
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