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Title: A novel bis-Lactonisation of naphtho- and phenanthro-1,2-dioxines with malonate nucleophiles
Authors: Greatrex, B.
Jevric, M.
Kimber, M.C.
Krivickas, S.J.
Taylor, D.K.
Tiekink, E.R.T. 
Keywords: bis-lactones
cis-γHydroxy enones
Domino reactions
Michael additions
Issue Date: 2003
Citation: 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.
Source Title: Synthesis
ISSN: 00397881
Appears in Collections:Staff Publications

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