Li Sha, Tang Ziwei, Wang Yang, Wang Dan, Wang Zhanlin, Yu Chenxia, Li Tuanjie, Wei Donghui, Yao Changsheng
Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science , Jiangsu Normal University , Xuzhou , Jiangsu 221116 , P R China.
The College of Chemistry and Molecular Engineering , Zhengzhou University , 100 Science Avenue , Zhengzhou , Henan 450001 , P R China.
Org Lett. 2019 Mar 1;21(5):1306-1310. doi: 10.1021/acs.orglett.8b04082. Epub 2019 Feb 15.
An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.
在温和条件下实现了氮杂环卡宾（NHC）催化的丙二烯酸酯与异吲哚酮之间的γ-特异性类羟醛反应，以中等至良好的产率、高非对映选择性和出色的原子经济性得到了带有异吲哚酮部分的三取代丙二烯衍生物。密度泛函理论（DFT）计算表明，γ-加合物的形成在能量上比α-加合物更有利。本文报道的结果为NHC促进的涉及丙二烯酸酯的反应开辟了一条新途径。
