Details

Autor(en) / Beteiligte

• Zhang, Ming
• Wang, Xiao‐Chen

Titel

Bifunctional Borane Catalysis of a Hydride Transfer/Enantioselective [2+2] Cycloaddition Cascade

Ist Teil von

• Angewandte Chemie International Edition, 2021-07, Vol.60 (31), p.17185-17190

Auflage

International ed. in English

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2021

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Herein, we present a mild and efficient method for synthesizing enantioenriched tetrahydroquinoline‐fused cyclobutenes through a cascade reaction between 1,2‐dihydroquinolines and alkynones with catalysis by chiral spiro‐bicyclic bisboranes. The bisboranes served two functions: first they catalyzed a hydride transfer to convert the 1,2‐dihydroquinoline substrate to a 1,4‐dihydroquinoline, and then they activated the alkynone substrate for an enantioselective [2+2] cycloaddition reaction with the 1,4‐dihydroquinoline generated in situ. A borane‐catalyzed cascade reaction between a benzyl‐protected 1,2‐dihydroquinoline and an alkynone has been developed. The reaction consists of hydride transfer and enantioselective [2+2] cycloaddition, which are both promoted by the spiro‐bicyclic bisborane catalysts.