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Expanding the scope of the Babler-Daubin oxidation : 1,3-oxidative transposition of secondary allylic alcohols

Killoran, PM, Rossington, SB, Wilkinson, JA and Hadfield, JA 2016, 'Expanding the scope of the Babler-Daubin oxidation : 1,3-oxidative transposition of secondary allylic alcohols' , Tetrahedron Letters, 57 (35) , pp. 3954-3957.

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Abstract

We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5 mol%) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents as well as a range of functional groups.

Item Type: Article
Schools: Schools > School of Environment and Life Sciences > Biomedical Research Centre
Journal or Publication Title: Tetrahedron Letters
Publisher: Elsevier
ISSN: 0040-4039
Related URLs:
Funders: Kidscan
Depositing User: JA Hadfield
Date Deposited: 03 Aug 2016 10:50
Last Modified: 15 Sep 2016 09:50
URI: http://usir.salford.ac.uk/id/eprint/39561

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