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

Killoran, PM; Rossington, SB; Wilkinson, JA; Hadfield, JA

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.

Citation

Killoran, P., Rossington, S., Wilkinson, J., & Hadfield, J. (2016). Expanding the scope of the Babler-Daubin oxidation : 1,3-oxidative transposition of secondary allylic alcohols. Tetrahedron Letters, 57(35), 3954-3957. https://doi.org/10.1016/j.tetlet.2016.07.076

• Journal Article Type: Article
• Acceptance Date: Jul 25, 2016
• Online Publication Date: Jul 26, 2016
• Publication Date: Aug 31, 2016
• Deposit Date: Aug 3, 2016
• Publicly Available Date: Jul 26, 2017
• Journal: Tetrahedron Letters
• Print ISSN: 0040-4039
• Publisher: Elsevier
• Volume: 57
• Issue: 35
• Pages: 3954-3957
• DOI: https://doi.org/10.1016/j.tetlet.2016.07.076
• Publisher URL: http://dx.doi.org/10.1016/j.tetlet.2016.07.076
• Related Public URLs: http://www.sciencedirect.com/science/journal/00404039