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|Title:||A novel bis-Lactonisation of naphtho- and phenanthro-1,2-dioxines with malonate nucleophiles|
|Source:||Greatrex, B.,Jevric, M.,Kimber, M.C.,Krivickas, S.J.,Taylor, D.K.,Tiekink, E.R.T. (2003). A novel bis-Lactonisation of naphtho- and phenanthro-1,2-dioxines with malonate nucleophiles. Synthesis (5) : 668-672. ScholarBank@NUS Repository.|
|Abstract:||Malonate nucleophiles add in a conjugate fashion to substituted naphtho- and phenanthro-1,2-dioxines to furnish functionalised bis-lactones in high yield and with high de. The basicity of the malonate nucleophile is sufficiently mild to rearrange the 1,2-dioxines to yield the transient cis-δhydroxy enone species with no further Kornblum-DeLaMare rearrangement. The cis-δhydroxy enones readily undergo conjugate addition by malonate nucleophiles in a highly diastereoselective fashion. An intramolecular domino cyclisation then ensues yielding the observed bis-lactones. The relative configuration of the bis-lactone series was established by 1- and 2-D 1H, 13C NMR techniques and further confirmed by single crystal X-ray analysis.|
|Appears in Collections:||Staff Publications|
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