Bismuth(III) Triflate-Catalyzed Synthesis of Substituted 2-Alkenylfurans

作者:Nitsch Dominik; Bach Thorsten*
来源:Journal of Organic Chemistry, 2014, 79(13): 6372-6379.
DOI:10.1021/jo5009993

摘要

A convergent synthesis of the title compounds is reported, which relies on a successive 2-fold S-N'-type substitution reaction at methoxy-substituted propargylic acetates. The furan C3-C4 bond is presumably established by silyl enol ether attack at a propargylic cation intermediate. The resulting alpha-methoxyallene is intramolecularly substituted, leading to cyclization by displacement of the methoxy group (O-C2 bond formation) and to simultaneous formation of the exocyclic alkene double bond. Despite the relatively mild conditions, the reactions were complete within 5 mm.

  • 出版日期2014-7-4