Facile generation of α-silyl carbanion of trimethylsilyl group assisted by intramolecular pyridyl group coordination

Kenichiro Itami, Koichi Mitsudo, Jun ichi Yoshida

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Novel methodology for the generation of α-silyl carbanion by the deprotonation of trimethylsilyl group with tert-butyllithium or LDA has been developed. This newly developed α-lithiation protocol is based on the intramolecular pyridyl group coordination to stabilize the α-silyl carbanion, together with the inherent silicon α effect. The importance of the use of the 2-pyridyl group in 'pyridyl'- and 'silyl'-directed α- lithiation has been confirmed by the control experiments utilizing phenyltrimethylsilane and (3-pyridyl)trimethylsilane.

Original languageEnglish
Pages (from-to)5533-5536
Number of pages4
JournalTetrahedron Letters
Issue number30
Publication statusPublished - Jul 1999
Externally publishedYes


ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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