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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Visible-Light-Promoted Oxidative [4 + 2] Cycloadditions of Aryl Silyl Enol Ethers
1Department of Chemistry, Zhejiang University , 866 Yuhangtang Road, Hangzhou 310058, China.
Abstract:
Visible-light-promoted oxidative [4 + 2] cycloadditions of ε,3-unsaturated silyl enol ethers have been developed to efficiently and diastereoselectively construct polycyclic skeletons under mild conditions. The diastereoselectivities were dependent on the stereoconfiguration of silyl enol ether, substitutions on the link, as well as electric properties of substitutions on aryl rings. The intermediates could be trapped by TEMPO, oxygen or methanol. Mechanistic studies indicated the reaction was initiated by one-electron oxidation of the silyl enol ether.
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