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Communication | Regular issue | Vol 96, No. 8, 2018, pp.1363-1372
Published online, 27th July, 2018
DOI: 10.3987/COM-18-13940
Lewis Acid Promoted Prins Cyclization Using Non-Conjugated Diene Alcohol: Sequential Reactions Terminated by Fluoride Ion

Kouichi Matsumoto,* Rina Yanagi, Kouji Yamaguchi, Erin Hayashi, Eri Yasuda, Kaho Kuriyama, Toshiki Nokami, Keiji Nishiwaki, and Shigenori Kashimura

*Faculty of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan

Abstract

The sequential cyclization involving Prins cyclization was successfully demonstrated, in which the various aldehydes bearing the alkyl or aromatic substituent were reacted with the alcohol bearing the non-conjugated diene moiety in the presence of 2 equiv. of BF3·Et2O and 4 mol% of TMSCl at -40 oC to afford the corresponding fluorinated bicyclic compounds in moderate to good yields.