Li Dongqiu, Wu Jiale, Yang LuLu, Cai Shuangshuang, Tang Yuhai, Li Yang, Xu Silong
School of Chemistry and Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, Xi'an 710049, P. R. China.
Northwest Rubber & Plastics Research & Design Institute Co., Ltd., Xianyang 712023, China.
Org Lett. 2025 Jan 10;27(1):51-56. doi: 10.1021/acs.orglett.4c03842. Epub 2024 Dec 20.
Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates with electron-poor alkenes , which affords exocyclic olefinic cyclohexenes in good yields and excellent regio-, diastereo-, and / selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates use the β- and ε-carbons for the bond formation, presenting new and regiodivergent C synthons for Lewis base-catalyzed annulations.
