4.8 Article

Highly Stereoselective 7-Endo-Trig/Ring Contraction Cascade To Construct Pyrrolo[1,2-a]quinoline Derivatives

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ORGANIC LETTERS
卷 12, 期 8, 页码 1696-1699

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AMER CHEMICAL SOC
DOI: 10.1021/ol100220c

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  1. National Natural Science Foundation of China [20702058, 20872157]
  2. Chinese Academy of Sciences [08QA14079]
  3. Shanghai Institute of Organic Chemistry

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With the cooperation of Cram's phenonium ion, a novel cascade reaction was illustrated to construct pyrrolo[1,2-a]quinolines as a sole diastereoisomer in good to excellent yields. Preliminary mechanistic studies revealed that the gamma-lactam ring and electron-rich arene are important driving forces for ring contraction.

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