Details

Autor(en) / Beteiligte

• Baker, Rachel J.
• Ching, Justin
• Hou, Teh Ren
• Franzoni, Ivan
• Lautens, Mark

Titel

Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring‐Opening

Ist Teil von

• Angewandte Chemie International Edition, 2022-02, Vol.61 (8), p.e202116171-n/a

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The dearomatization of 2‐naphthols represents a simple method for the construction of complex 3D structures from simple planar starting materials. We describe a cyclopropanation of 2‐naphthols that proceeds via cyclopropene ring‐opening using rhodium and acid catalysis under mild conditions. The vinyl cyclopropane molecules were formed with high chemoselectivity and scalability, which could be further functionalized at different sites. Both computational and experimental evidence were used to elucidate the reaction mechanism. The rhodium‐ and acid‐catalyzed dearomative cyclopropanation of naphthols from cyclopropene ring‐opening has been described. The reaction is scalable and highly chemoselective, and the vinyl cyclopropane products can be uniquely diversified. Experimental and computational studies support the proposed mechanism.