Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis

Takuya Nakagiri, Masahito Murai, Kazuhiko Takai

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The combination of a catalytic amount of Re2O7 and triphenyl phosphite as a reductant is effective for the deoxygenation of unactivated aliphatic epoxides to alkenes. The reaction proceeds stereospecifically with variously substituted epoxides under neutral conditions and is compatible with various functional groups. Protection and deprotection of a double bond functionality using an epoxide are shown as an example of the current rhenium-catalyzed deoxygenation protocol. The effect of reductants for the stereoselectivity has also been studied, indicating that the use of electron-deficient phosphines or phosphites is the key for the stereospecific deoxygenation. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)3346-3349
Number of pages4
JournalOrganic Letters
Volume17
Issue number13
DOIs
Publication statusPublished - Jul 2 2015

Fingerprint

deoxygenation
Rhenium
epoxy compounds
Epoxy Compounds
rhenium
Alkenes
Catalysis
alkenes
catalysis
Reducing Agents
Phosphines
Phosphites
Stereoselectivity
phosphines
Functional groups
Electrons
electrons

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis. / Nakagiri, Takuya; Murai, Masahito; Takai, Kazuhiko.

In: Organic Letters, Vol. 17, No. 13, 02.07.2015, p. 3346-3349.

Research output: Contribution to journalArticle

Nakagiri, Takuya ; Murai, Masahito ; Takai, Kazuhiko. / Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis. In: Organic Letters. 2015 ; Vol. 17, No. 13. pp. 3346-3349.
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