文献类型：期刊文献

英文题名：Palladium-catalyzed [6+4] cycloaddition with π-allyl all-carbon 1,6-dipole for the synthesis of ten-membered heterocycles

作者：Chen, Jun-Tao[1,2];Lin, Na[1];Xu, Linli[1];Wang, Yi[2];Luo, Xiaoyan[2];Liu, Yang-Zi[1];Deng, Wei-Ping[1,2]

机构：[1]Zhejiang Normal Univ, Dept Chem, Minist Educ Adv Catalysis Mat, Key Lab, 688 Yingbin Rd, Jinhua 321004, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Me, Sch Pharm, Shanghai 200237, Peoples R China

年份：2024

卷号：11

期号：5

外文期刊名：ORGANIC CHEMISTRY FRONTIERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001135633300001)】；

基金：This work was supported by the Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang (2022R01007), Start-up Research Grant from Zhejiang Normal University, the National Key Research and Development Program of China (2021YFA0804900), the NSFC (22201253), and Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism.

语种：英文

摘要：This paper presents the design and synthesis of a novel alpha,alpha-diester-delta-vinylvalerolactone, utilized as a new all-carbon dipolar precursor in a palladium-catalyzed [6 + 4] cycloaddition reaction with azadienes. The reaction results in the formation of a ten-membered heterocycle with up to 95% yield and exclusive regioselectivity. The method features mild reaction conditions and excellent functional group tolerance. The practical applicability of the synthesis is demonstrated through scale-up reactions and further transformation. This work introduces a novel alpha,alpha-diester-delta-vinylvalerolactone as a dipolar precursor in a palladium-catalyzed [6 + 4] cycloaddition reaction with azadienes, resulting in the production of ten-membered heterocycles.