Huang Group
School of Chemical Biology & Biotechnology

Hu Chen’s work has been published in J.Org.Chem.! Congratulations!

时间:2013-04-09

 

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Highly trans-Stereoselective Synthesis of Bicyclic Isoxazolidines via Copper-Catalyzed Triple Cascade Catalysis

 Hu Chen, Zhaofeng Wang, Yingnan Zhang, and Yong Huang*

J. Org. Chem., 2013, 78, 3503-3509.

A triple cascade was developed using a simple copper catalyst to trans-selectively access bicyclic isoxazolidines in a one-pot synthesis. This strategy features the in situ generation of nitrones and subsequent trapping by [3 + 2] cycloaddition. In this method, copper serves three catalytic functions: as a Lewis acid for the ene reaction, as an organometallic for aerobic oxidation, and as a Lewis acid for an endo-selective [3 + 2] cycloaddition. The successful merging of aerobic oxidation and Lewis acid catalysis demonstrated efficient cascade synergy.

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