Enantiospecific Brook Rearrangement of Tertiary Benzylic alpha-Hydroxysilanes

Juan F. Collados, Pablo Ortiz, Juana M. Pérez, Yiyin Xia, Mark A. J. Koenis, Wybren J. Buma, Valentin P. Nicu, Syuzanna R. Harutyunyan*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

4 Citations (Scopus)
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Abstract

The Brook rearrangement of simple, chiral tertiary benzylic -hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-Brook rearrangement can be followed by trapping of methyl or allyl electrophiles even in the protic environment, although with minimal retention of chirality.

Original languageEnglish
Pages (from-to)3900-3903
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number29
Early online date19-Jan-2018
DOIs
Publication statusPublished - 7-Aug-2018

Keywords

  • Synthetic methods
  • Rearrangement
  • Hydroxysilanes
  • Enantiospecific
  • Chirality
  • ABSOLUTE-CONFIGURATION
  • ANIONIC REARRANGEMENTS
  • CHIRAL MOLECULES
  • STEREOCHEMISTRY
  • SILYLCARBINOL
  • ALKOXYSILANE
  • ACYLSILANES
  • REDUCTION
  • ACYLATION
  • CARBON

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