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Au(I)-catalyzed synthesis of 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization.

Research paper by Jaya Kishore JK Vandavasi, Wan-Ping WP Hu, Siva Senthil Kumar SS Boominathan, Bing-Chun BC Guo, Cheng-Tien CT Hsiao, Jeh-Jeng JJ Wang

Indexed on: 07 Jul '15Published on: 07 Jul '15Published in: Chemical Communications



Abstract

A sustainable and simple Au(I) catalytic system to synthesise 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization is described. The key advantages of this reaction are selectivity, good functional group tolerance and a new approach for synthesis of oxabicyclic and oxatricyclic systems.