Carbocyclic Ring Closure of Aryl C‑Glycosides Promoted by Fluoroboric Acid

Carbocyclic Ring Closure of Aryl C‑Glycosides Promoted by Fluoroboric Acid

A novel transformation from rhamnose-type C-glycosides to 2-cyclopentenones is described. With the promotion of fluoroboric acid, C-glycosides underwent ring opening and subsequent Nazarov cyclization to afford 2-cyclopentenones in good to excellent yields. The solvent and the concentration of acid...

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Veröffentlicht in:Journal of organic chemistry 2020-07, Vol.85 (14), p.9339-9346
Hauptverfasser: Zheng, Qiannan, Tang, Shengbiao, Xiong, De-Cai, Li, Qin, Ye, Xin-Shan
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Zusammenfassung:A novel transformation from rhamnose-type C-glycosides to 2-cyclopentenones is described. With the promotion of fluoroboric acid, C-glycosides underwent ring opening and subsequent Nazarov cyclization to afford 2-cyclopentenones in good to excellent yields. The solvent and the concentration of acid are crucial to the yield of this transformation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00784