Molybdenum-Catalyzed Stereospecific Deoxygenation of Epoxides to Alkenes

Sobi Asako; Takahisa Sakae; Masahito Murai; Kazuhiko Takai

doi:10.1002/adsc.201600840

Molybdenum-Catalyzed Stereospecific Deoxygenation of Epoxides to Alkenes

Sobi Asako, Takahisa Sakae, Masahito Murai, Kazuhiko Takai

School of Engineering

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

Mild and simple catalytic systems consisting of molybdenum(VI) dichloride dioxide [MoO₂Cl₂] as a catalyst and a phosphine as reductant have been developed for the stereospecific deoxygenation of epoxides to alkenes. The reactions using 1,2-bis(diphenylphosphino)ethane (dppe) and triphenylphosphine (PPh₃) proceed with retention and inversion of stereochemistry, respectively. The mild reaction tolerates the presence of various functional groups and affords stereodefined substituted olefins in good yields. (Figure presented.).

Original language	English
Pages (from-to)	3966-3970
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	358
Issue number	24
DOIs	https://doi.org/10.1002/adsc.201600840
Publication status	Published - Dec 22 2016

Keywords

alkenes
deoxygenation
epoxides
molybdenum
stereospecific process

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201600840

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title = "Molybdenum-Catalyzed Stereospecific Deoxygenation of Epoxides to Alkenes",

abstract = "Mild and simple catalytic systems consisting of molybdenum(VI) dichloride dioxide [MoO2Cl2] as a catalyst and a phosphine as reductant have been developed for the stereospecific deoxygenation of epoxides to alkenes. The reactions using 1,2-bis(diphenylphosphino)ethane (dppe) and triphenylphosphine (PPh3) proceed with retention and inversion of stereochemistry, respectively. The mild reaction tolerates the presence of various functional groups and affords stereodefined substituted olefins in good yields. (Figure presented.).",

keywords = "alkenes, deoxygenation, epoxides, molybdenum, stereospecific process",

author = "Sobi Asako and Takahisa Sakae and Masahito Murai and Kazuhiko Takai",

note = "Funding Information: We thank MEXT for financial support, and KAKENHI Grant-in-Aid for Scientific Research (A) No. 26248030. Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Molybdenum-Catalyzed Stereospecific Deoxygenation of Epoxides to Alkenes

AU - Asako, Sobi

AU - Sakae, Takahisa

AU - Murai, Masahito

AU - Takai, Kazuhiko

PY - 2016/12/22

Y1 - 2016/12/22

N2 - Mild and simple catalytic systems consisting of molybdenum(VI) dichloride dioxide [MoO2Cl2] as a catalyst and a phosphine as reductant have been developed for the stereospecific deoxygenation of epoxides to alkenes. The reactions using 1,2-bis(diphenylphosphino)ethane (dppe) and triphenylphosphine (PPh3) proceed with retention and inversion of stereochemistry, respectively. The mild reaction tolerates the presence of various functional groups and affords stereodefined substituted olefins in good yields. (Figure presented.).

AB - Mild and simple catalytic systems consisting of molybdenum(VI) dichloride dioxide [MoO2Cl2] as a catalyst and a phosphine as reductant have been developed for the stereospecific deoxygenation of epoxides to alkenes. The reactions using 1,2-bis(diphenylphosphino)ethane (dppe) and triphenylphosphine (PPh3) proceed with retention and inversion of stereochemistry, respectively. The mild reaction tolerates the presence of various functional groups and affords stereodefined substituted olefins in good yields. (Figure presented.).

KW - alkenes

KW - deoxygenation

KW - epoxides

KW - molybdenum

KW - stereospecific process

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Molybdenum-Catalyzed Stereospecific Deoxygenation of Epoxides to Alkenes

Abstract

Keywords

ASJC Scopus subject areas

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