Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols | Zendy

Natalie J. Capel | Zendy; Martin R. Lindley | Zendy; Gareth J. Pritchard | Zendy; Marc C. Kimber | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols

Author(s) -

Natalie J. Capel,

Martin R. Lindley,

Gareth J. Pritchard,

Marc C. Kimber

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b03118

Subject(s) - indium , isomerization , aldehyde , substrate (aquarium) , chemistry , trifluoromethanesulfonate , cope rearrangement , solvent , photochemistry , medicinal chemistry , catalysis , organic chemistry , oceanography , geology

An indium-mediated isomerization of 1,4-dienols to 1,3-dienols is described. This procedure consists of the addition of pentadienylindium, in a protic solvent, to aldehydes giving the kinetic γ-allylation product in high yields. The subsequent conversion of this γ-allylation product to its thermodynamic 1,3-dienol α-isomer can be achieved by its exposure to indium triflate in the presence of a substoichiometric amount of aldehyde at room temperature. This transformation exhibited moderate to good substrate scope and has been shown to proceed by a 2-oxonia Cope rearrangement.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research