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Regioselectivity in the ene reaction of singlet oxygen with ortho-prenylphenol derivatives

By J.J. Helesbeux, O. Duval, D. Guilet, D. Seraphin, D. Rondeau and P. Richomme


The ene reaction of singlet oxygen with prenylated dihydroxyacetophenones led to the 2-hydroperoxy-3-methylbut-3-enyl derivatives as the major product. This original regioselectivity outlined a new effect, in competition with the previously established large group non-bonding effect. The oxidation products distribution could be explained by a stabilising interaction between the phenolic hydrogen, ortho to the prenyl side chain, and the perepoxide intermediate

Topics: large group effect, phenolic assistance, prenyl chain, regioselectivity, Schenck ene reaction
Publisher: 'Elsevier BV'
Year: 2003
DOI identifier: 10.1016/S0040-4020(03)00733-6
OAI identifier:
Provided by: Okina

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