Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis

Takuya Nakagiri; Masahito Murai; Kazuhiko Takai

doi:10.1021/acs.orglett.5b01583

Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis

Takuya Nakagiri, Masahito Murai, Kazuhiko Takai

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35 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 language	English
Pages (from-to)	3346-3349
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.5b01583
Publication status	Published - Jul 2 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis",

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).",

author = "Takuya Nakagiri and Masahito Murai and Kazuhiko Takai",

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AU - Nakagiri, Takuya

AU - Murai, Masahito

AU - Takai, Kazuhiko

PY - 2015/7/2

Y1 - 2015/7/2

N2 - 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).

AB - 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).

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Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis

Abstract

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