Details

Autor(en) / Beteiligte

• Xun, Shan-Shan
• Wang, Han
• Yu, Chang-Bin
• Lu, Sheng-Mei
• Zhou, Yong-Gui

Titel

Diarylborinic Acid-Catalyzed Ring Opening of cis-4-Hydroxymethyl-1,2-Cyclopentene Oxides: Synthesis of 1,2,4-Trisubstituted Cyclopentanes

Ist Teil von

• Organic letters, 2023-10, Vol.25 (41), p.7540-7544

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2023

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A diarylborinic acid-catalyzed ring opening of cis-4-hydroxymethyl-1,2-cyclopentene oxides was developed with N-nucleophiles including anilines, benzotriazole, and alkylamines, as well as S-nucleophiles, affording 1,2,4-trisubstituted cyclopentane compounds containing a quaternary carbon center. The mechanism study indicated that the “half-cage” structure formed by the epoxide substrate and the catalyst prevents the nucleophiles from attacking the inner side of the “half-cage”, resulting in the desired ring-opening product.