The Journal of organic chemistry

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

D Nitsch, T Bach

Index: Nitsch, Dominik; Huber, Stefan M.; Poethig, Alexander; Narayanan, Arjun; Olah, George A.; Prakash, G. K. Surya; Bach, Thorsten Journal of the American Chemical Society, 2014 , vol. 136, # 7 p. 2851 - 2857

Full Text: HTML

Citation Number: 12

Abstract

A convergent synthesis of the title compounds is reported, which relies on a successive 2- fold SN′-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 α-methoxyallene is intramolecularly substituted, leading to cyclization by displacement of the methoxy group (O–C2 bond formation) and to ...