Asymmetric retro-[1,4] brook rearrangement and its stereochemical course at silicon

Atsuo Nakazaki, Takeshi Nakai, Katsuhiko Tomooka

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

(Chemical Equation Presented) Taking the silyl group a step further: An unprecedented rearrangement in an anion derived from an allyloxysilane occurs by a [1,4] shift of the silyl group (see scheme). The asymmetric synthesis of enantiomerically enriched γ-functionalized allylsilanes with Si stereocenters can be accomplished with this retro-[1,4] Brook rearrangement. E = electrophile.

Original languageEnglish
Pages (from-to)2235-2238
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number14
DOIs
Publication statusPublished - Mar 27 2006
Externally publishedYes

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Silicon
Anions
Negative ions
allylsilane

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Asymmetric retro-[1,4] brook rearrangement and its stereochemical course at silicon. / Nakazaki, Atsuo; Nakai, Takeshi; Tomooka, Katsuhiko.

In: Angewandte Chemie - International Edition, Vol. 45, No. 14, 27.03.2006, p. 2235-2238.

Research output: Contribution to journalArticle

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