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Gold-Catalyzed Oxidative Cyclization of Chiral Homopropargyl Amides: Synthesis of Enantioenriched γ-Lactams

Chao Shu , Meng-Qi Liu, Shan-Shan Wang, Long Li and Long-Wu Ye*

*Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, PR China, Email:

C. Shu, M.-Q. Liu, S.-S. Wang, L. Li, L.-W. Ye, J. Org. Chem., 2013, 78, 3292-3299.

DOI: 10.1021/jo400127x

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A gold-catalyzed tandem cycloisomerization/oxidation of homopropargyl amides provides ready access to synthetically useful chiral γ-lactams with excellent ee by combining the chiral tert-butylsulfinimine chemistry and gold catalysis. The use of readily available starting materials, a simple procedure, and mild reaction conditions are other significant features of this method.

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The ee for the PMP-substituted substrate probably decreases due to the formation of a carbocation under the acidic reaction conditions.

Long-Wu Ye, May 3, 2014

Key Words

γ-lactams, MCPBA

ID: J42-Y2013-0830