文献类型：期刊文献

英文题名：Sulfone as a Transient Activating Group in the Palladium-Catalyzed Asymmetric [4+3] Cycloaddition of Trimethylenemethane Enabling the Enantioselective Synthesis of Fused Azepines

作者：Liu, Yang-Zi[1];Wang, Zhongao[2,3];Huang, Zesheng[2,3];Yang, Wu-Lin[2,3];Deng, Wei-Ping[2,3,4]

机构：[1]Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[4]Zhejiang Normal Univ, Dept Chem, Minist Educ Adv Catalysis Mat, Key Lab, Jinhua 321004, Zhejiang, Peoples R China

年份：2021

卷号：23

期号：3

起止页码：948

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000629001700060)】；

基金：This work is supported by the National Natural Science Foundation of China (no. 21971062). We thank the Research Center of Analysis and Test of East China University of Science and Technology for their help with the NMR and HRMS analysis.

语种：英文

摘要：The palladium-catalyzed asymmetric [4 + 3] cycloaddition of a sulfonyl-trimethylenemethane (TMM) donor with azadienes furnished various sulfonyl-fused azepines with exclusive regioselectivities and excellent stereoselectivities (up to >20:1 dr, >99% ee) in high yields (up to 93%). Moreover, sulfone, serving as a transient activating group of the TMM species, can be easily removed from the cycloadducts to provide the structurally simple fused azepines with excellent enantioselectivities. This strategy demonstrates sulfonyl-TMM as an effective surrogate of naked TMM with high reactivity, exclusive regioselectivity, and excellent stereoselectivity.