Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach

Daniel J. MacK, Boying Guo, Jon T Njardarson

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Unsaturated cyclic ethers can be mildly and selectively reduced with catalytic amounts of B(C 6F 5) 3 in the presence of an alkylsilane. The allylic position is preferentially reduced with minimal or no scrambling of olefin geometry. For electronically equivalent substrates, steric factors guide the reducing agent to the least substituted site. This journal is

Original languageEnglish (US)
Pages (from-to)7844-7846
Number of pages3
JournalChemical Communications
Volume48
Issue number63
DOIs
StatePublished - Aug 14 2012

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Cyclic Ethers
Reducing Agents
Alkenes
Reducing agents
Olefins
Ethers
Alcohols
Geometry
Substrates
allyl alcohol

ASJC Scopus subject areas

  • Metals and Alloys
  • Materials Chemistry
  • Surfaces, Coatings and Films
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Catalysis
  • Chemistry(all)

Cite this

Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach. / MacK, Daniel J.; Guo, Boying; Njardarson, Jon T.

In: Chemical Communications, Vol. 48, No. 63, 14.08.2012, p. 7844-7846.

Research output: Contribution to journalArticle

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