Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

Open Access
Authors
  • J.F. Collados
  • P. Ortiz
  • J.M. Pérez
  • Y. Xia
Publication date 07-08-2018
Journal European Journal of Organic Chemistry
Volume | Issue number 2018 | 29
Pages (from-to) 3900-3903
Number of pages 4
Organisations
  • Faculty of Science (FNWI) - Van 't Hoff Institute for Molecular Sciences (HIMS)
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.
Document type Article
Note With supplementary file
Language English
Published at https://doi.org/10.1002/ejoc.201701469
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