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

Shih Fan Hsu, Chih Wei Ko, Yao Ting Wu

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1756-1762
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number10
DOIs
Publication statusPublished - 2011 Jul 1

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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