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

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• 作者：Hu Chen ; Zhaofeng Wang ; Yingnan Zhang ; Yong Huang
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：78
• 期：7
• 页码：3503-3509
• 全文大小：362K
• 年卷期：v.78,no.7(April 5, 2013)
• ISSN：1520-6904

文摘

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.