Regio- and Stereoselective Monoepoxidation of Dienes using Methyltrioxorhenium: Synthesis of Allylic Epoxides | Zendy

Saroj Ranjan De | Zendy; Ganesh Kumar | Zendy; Jawahar L. Jat | Zendy; Saritha Birudaraju | Zendy; Biao Lu | Zendy; R Manne | Zendy; P. Narender | Zendy; Adeniyi Michael Adebesin | Zendy; John R. Falck | Zendy

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Regio- and Stereoselective Monoepoxidation of Dienes using Methyltrioxorhenium: Synthesis of Allylic Epoxides

Author(s) -

Saroj Ranjan De,

Ganesh Kumar,

Jawahar L. Jat,

Saritha Birudaraju,

Biao Lu,

R Manne,

P. Narender,

Adeniyi Michael Adebesin,

John R. Falck

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo501958d

Subject(s) - regioselectivity , chemistry , allylic rearrangement , olefin fiber , stereoselectivity , conjugated system , silylation , catalysis , pyridine , organic chemistry , stereochemistry , polymer

Methyltrioxorhenium (MTO) complexed with pyridine was shown to be a highly effective catalyst for the regioselective monoepoxidation of conjugated di- and trienes using 30% H2O2 at or below room temperature. The resultant allylic epoxides, and the triols derived from them, are versatile synthetic intermediates as well as substructures present in many bioactive natural products. The site of epoxidation was dependent upon olefin substitution, olefin geometry (Z vs E), and the presence of electron-withdrawing substituents on adjacent carbons. For 1-acyl(silyl)oxypenta-2,4-dienes, epoxidation of the distal olefin was generally favored in contrast to the adjacent regioselectivity characteristic of Sharpless, peracid, and other directed epoxidations of hydroxylated dienes.

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