Abstract
We report the isomerisation of α,β-unsaturated diesters to thermodynamically less favourable β,γ-unsaturated carbonyl compounds in the absence of strongly basic anhydrous or photochemical conditions. Stereoselective deconjugative isomerisation provides E-selective β,γ-unsaturated diesters via an enolate intermediate generated in situ from α,β-unsaturated diesters with high yield and stereoselectivity. Based on density functional theory calculations, the origin of the E-selective deconjugation pathway from conjugated compounds has been elucidated.
Original language | English |
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Pages (from-to) | 3427-3433 |
Number of pages | 7 |
Journal | Organic Chemistry Frontiers |
Volume | 7 |
Issue number | 21 |
DOIs | |
State | Published - 7 Nov 2020 |
Bibliographical note
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