Carboxylation with CO2 via Brook rearrangement: preparation of α-hydroxy acid derivatives

Org Lett. 2014 Jan 3;16(1):14-7. doi: 10.1021/ol403099f. Epub 2013 Dec 6.

Abstract

In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Carbon Dioxide / chemistry*
  • Hydroxy Acids / chemical synthesis*
  • Hydroxy Acids / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry

Substances

  • Aldehydes
  • Hydroxy Acids
  • Organometallic Compounds
  • Carbon Dioxide