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- Title
Asymmetric Phosphoric Acid‐catalyzed Aza‐Friedel–Crafts Reaction of Furan with Cyclic N‐Sulfimines.
- Authors
Lee, Jiseon; Kim, Sung‐Gon
- Abstract
Highlights from the article: In contrast, the asymmetric catalytic Friedel-Crafts reactions of furans has been less extensively studied than those of indole and its derivatives. Herein, we demonstrate the first enantioselective aza-Friedel-Crafts reaction of furans with cyclic I N i -sulfimines catalyzed by a chiral Brønsted phosphoric acid ( B PA b ). Based on our previous asymmetric catalytic aza-Friedel-Crafts reaction of cyclic I N i -sulfimines,[5] SP c,d sp we first evaluated a chiral BINOL-derived phosphoric acid (Figure)[7] as a catalyst for the asymmetric Friedel-Crafts reaction of benzoxathiazine 2,2-dioxide B 1a b with 2-methoxyfuran B 2 b . In conclusion, we have developed an asymmetric aza-Friedel-Crafts alkylation reaction between cyclic I N i -sulfimines and 2-methoxyfuran B . b Chiral BINOL-derived phosphoric acid was used as an organocatalyst and the reactions were tolerant to various cyclic I N i -sulfimines, providing access to methoxyfuran-2-yl sulfamidate derivatives in good yields with moderate to high enantioselectivities (up to 94:6 er).
- Subjects
FURANS synthesis; ELECTRON-deficient compounds; METHOXY group; FRIEDEL-Crafts reaction; NICOTINIC acetylcholine receptors
- Publication
Bulletin of the Korean Chemical Society, 2019, Vol 40, Issue 6, p606
- ISSN
0253-2964
- Publication type
Article
- DOI
10.1002/bkcs.11731