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NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ‑Functionalized Allenoates

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journal contribution
posted on 15.02.2019, 15:33 by Sha Li, Ziwei Tang, Yang Wang, Dan Wang, Zhanlin Wang, Chenxia Yu, Tuanjie Li, Donghui Wei, Changsheng Yao
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.