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Complete switch of migratory aptitude in aluminum-catalyzed 1,2-rearrangement of differently α,α-disubstituted a-siloxy aldehydes

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) Control of the migration tendency: The regiodivergent 1,2-rearrangement of asiloxy aldehydes bearing α-aryl and α-alkyl substituents into α-siloxy ketones has been realized by using different aluminum Lewis acid catalyst/solvent systems (see scheme). The scope of this unprecedented protocol has been investigated with various substrates and clearly demonstrates its utility for the selective synthesis of two structural isomers from one substrate.

Original languageEnglish
Pages (from-to)5203-5206
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number28
DOIs
Publication statusPublished - 2008 Jun 27
Externally publishedYes

Keywords

  • Aluminum
  • Lewis acids
  • Rearrangement
  • Regioselectivity
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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