Directed intermolecular carbomagnesation across vinylsilanes: 2-PyMe2Si group as a removable directing group

Kenichiro Itami, Koichi Mitsudo, Jun Ichi Yoshida

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44 Citations (Scopus)

Abstract

Facile addition of primary alkyl Gridnard reagents to vinylsilanes has been realized for the first time by exploiting the directing effect of a 2-pridyl group on silicon [Eq. (1)]. Three-component coupling reactions of a Grignard reagent, the vinylsilane, and an electrophile, followed by oxidative removal of the 2-pyridyldimethylsilyl group with H2O2 furnishes various secondary alcohols in excellent overall yields.

Original languageEnglish
Pages (from-to)2337-2339
Number of pages3
JournalAngewandte Chemie - International Edition
Volume40
Issue number12
DOIs
Publication statusPublished - Jun 18 2001
Externally publishedYes

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Keywords

  • Alcohols
  • Magnesium
  • Multicomponent reactions
  • Silicon
  • Synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)

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