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https://hdl.handle.net/2440/18021
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Type: | Journal article |
Title: | A novel bis-lactonisation of naphtho- and phenanthro-1,2-dioxines with malonate nucleophiles |
Author: | Greatrex, B. Jevric, M. Kimber, M. Krivickas, S. Taylor, D. Tiekink, E. |
Citation: | Synthesis: journal of synthetic organic chemistry, 2003; 2003(5):668-672 |
Publisher: | Georg Thieme Verlag KG |
Issue Date: | 2003 |
ISSN: | 0039-7881 1437-210X |
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, [1][3]C NMR techniques and further confirmed by single crystal X-ray analysis. |
DOI: | 10.1055/s-2003-38073 |
Published version: | https://www.thieme-connect.com/ejournals/abstract/synthesis/doi/10.1055/s-2003-38073 |
Appears in Collections: | Aurora harvest 6 Chemistry publications |
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