4.6 Article

One-step chemoselective conversion of tetrahydropyranyl ethers to silyl-protected alcohols

Journal

RSC ADVANCES
Volume 4, Issue 28, Pages 14475-14479

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ra00655k

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Funding

  1. University of Santiago de Compostela
  2. Center for Research in Biological Chemistry and Molecular Materials (CIQUS)
  3. Ministry of Economy and Competitiveness
  4. Xunta de Galicia

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Aluminium trichloride catalyses the expeditious direct conversion of tetrahydropyranyl ethers to silyl ethers. This one-step transformation is chemoselective versus deprotection of the acetal and hydrosilylation of unsaturated carbon-carbon bonds, and can also be applied to linear acetals. A possible mechanism is tentatively proposed.

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