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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Pd-catalyzed asymmetric (6+2) dipolar cyclization for medium-sized spirooxindoles
Yu-Qing Xiao1, Zi-Qing Li1, Fang Hu2
1CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China. luliangqiu@ccnu.edu.cn.
Abstract:
Chiral spirooxindoles are privileged scaffolds in bioactive molecules, yet efficient strategies for their functionalization-especially for medium-sized spirocycles-remain scarce. We report a Pd-catalyzed asymmetric (6+2) dipolar cyclization between vinyloxetanes and 3-diazoquinoline-2,4-diones, which allows the synthesis of enantioenriched spirooxindoles with eight-membered lactones under mild conditions. This method provides 22 examples with high yields and enantioselectivities (up to 90% yield and 98% ee), facilitated by a tailored chiral phosphine ligand and in situ photogenerated ketene dipolarophiles.
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