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Alkylideneindoleninium Ions and Alkylideneindolenines: Key Intermediates for the Asymmetric Synthesis of 3-Indolyl Derivatives

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 3, Issue 10, Pages 1036-1052

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201402093

Keywords

alkylideneindolenines; alkylideneindoleninium ions; 1,4-conjugate addition; indoles; vinyl imines

Funding

  1. National Natural Science Foundation of China [21102142]
  2. Outstanding Young Scientist Award Foundation of Shandong Province [BS2013YY002]
  3. Qingdao Special Research Foundation of Science and Technology [14-2-4-70-jch]
  4. Talents of High Level Scientific Research Foundation of Qingdao Agricultural University [631223]

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Alkylideneindoleninium ions and alkylideneindolenines generated from 3-substituted indoles are important intermediates in organic synthesis, which can be trapped by a large variety of nucleophilic reagents to construct biologically important 3-indolyl derivatives. This Focus Review summarizes the recent developments in asymmetric syntheses of 3-indolyl derivatives via alkylideneindoleninium ions or alkylideneindolenines. The elimination mechanism of leaving groups and asymmetric strategies are discussed.

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