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 -γ-hydroxy enone species
with no further Kornblum-DeLaMare rearrangement. The cis -γ-hydroxy 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 1 H, 13 C
NMR techniques and further confirmed by single crystal X-ray analysis.
Key words
bis -lactones - peroxides -
cis -γ-Hydroxy enones - domino reactions - michael additions
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