Cobalt-catalyzed carbon-carbon bond formation: Synthesis and applications of enantiopure pyrrolidine derivatives[1]

Shih Fan Hsu, Chih Wei Ko, Yao Ting Wu

研究成果: Article

22 引文 斯高帕斯(Scopus)

摘要

In the presence of cobalt catalysts and tetramethylethylenediamine (TMEDA), the iodine atom in (S)-2-(iodomethyl)pyrrolidines was replaced by an aryl or an alkynyl group from the corresponding Grignard reagent, and the coupling products were obtained in good to excellent yields (16 examples; 75-94% yields). The scope and limitations of this protocol were examined. The stereochemistry of the pyrrolidines was unaffected by the reaction conditions. The coupling products are important building blocks of phenanthroindolizidine alkaloids. Palladium-catalyzed formal [4+2] cycloaddition of 2,2′-diiodobiphenyl with the thus-generated (S)-2-(3-trimethylsilyl-2-propynyl)pyrrolidine gave a good yield of the desilylated phenanthrene, which was then converted into unnatural (+)-(S)-tylophorine by the Pictet-Spengler cyclization.

原文English
頁(從 - 到)1756-1762
頁數7
期刊Advanced Synthesis and Catalysis
353
發行號10
DOIs
出版狀態Published - 2011 七月 1

    指紋

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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