Organocatalytic Friedel-Crafts Alkylation/Lactonization Reaction of Naphthols with 3-Trifluoroethylidene Oxindoles: The Asymmetric Synthesis of Dihydrocoumarins was written by Zhao, Yun-Long;Lou, Qin-Xin;Wang, Long-Sheng;Hu, Wen-Hui;Zhao, Jun-Ling. And the article was included in Angewandte Chemie, International Edition in 2017.Computed Properties of C8H6BrNO This article mentions the following:
Naphthols and 3-trifluoroethylidene oxindoles were found to undergo an asym. Friedel-Crafts alkylation/lactonization reaction, catalyzed by only 2.5 mol % of a quinine-derived squaramide catalyst, to afford the corresponding 婵?aryl-闁?trifluoromethyl dihydrocoumarin derivatives I (R1 = H, 5-Me, 5-Cl, 5-Br, 7-F, 7-Br; R2 = H, 6-MeO, 6-OBn, 6-Ph, etc.) in high yields (up to 99 %) with excellent enantio- and diastereoselectivities (up to 98 % ee, >20:1 d.r.). Importantly, the lactonization proceeded by nucleophilic attack of the naphthol hydroxy group at the amide motif of the oxindoles under mild reaction conditions. This protocol represents a new strategy for the formation of dihydrocoumarins by an efficient intramol. amide C-N bond-cleavage and esterification process. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8Computed Properties of C8H6BrNO).
7-Bromooxindole (cas: 320734-35-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Computed Properties of C8H6BrNO
Referemce:
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