Catalytic Asymmetric[3+2]Cycloaddition of Exocyclic Enol Ethers for the Synthesis of Spiroketals  

作　　者：Fengcai Zhang Yuqiao Zhou Hansen Zhao Long Chen Weidi Cao Xiaoming Feng 

机构地区：[1]Key Laboratory of Green Chemistry and Technology,Ministry of Education,College of Chemistry,Sichuan University,Chengdu 610064,China

出　　处：《Precision Chemistry》2023年第7期423-428,共6页精准化学（英文）

基　　金：the National Natural Science Foundation of China(Nos.21890723 and 21921002);the Science and Technology Department of Sichuan Province(Nos.2021YJ0561)for financial support.

摘　　要：An efficient synthesis of chiral benzannulated spiroketals via catalytic asymmetric[3+2]cycloaddition of exocyclic enol ethers with p-quinones was achieved.The transformation was enabled by a chiral N,N′-dioxides/Tm^(Ⅲ)complex as the Lewis acid catalyst and afforded a series of enantiomerically enriched benzannulated spiroketal derivatives in good yields(up to 99%)and enantioselectivities(up to 98%ee).Topographic steric maps and distribution of the buried volumes of the catalysts via Cavallo’s SambVca 2 tool were used to elucidate the enantioinduction raised by the ligands and the metal ions.

关 键 词：asymmetric catalysis [3+2]-cycloaddition SPIROKETALS exocyclic enol ethers QUINONES 

分 类 号：O626[理学—有机化学]