Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol, is researched, Molecular C20H12Br2O2, CAS is 119707-74-3, about Dianionic Phase-Transfer Catalyst for Asymmetric Fluoro-cyclization.Quality Control of (S)-3,3′-Dibromo-1,1′-bi-2-naphthol.
Inspired by the dicationic nature of the electrophilic fluorinating reagent, Selectfluor, we rationally designed a series of dicarboxylic acid precatalysts, which, when deprotonated, act as anionic phase-transfer catalysts for asym. fluorination of alkenes. Among them, I (n = 1) having the shortest linker moiety efficiently catalyzed unprecedented 6-endo-fluoro-cyclization of various allylic amides, affording fluorinated dihydrooxazine compounds with high enantioselectivity (up to 99% ee). In addition to cyclic substrates, acyclic trisubstituted alkenes underwent the reaction with good diastereoselectivity, whereas low diastereoselectivity was observed for linear disubstituted alkenes. Results suggest that the reaction proceeds via a fluoro-carbocation intermediate.
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Reference:
Bromide – Wikipedia,
bromide – Wiktionary