Trialkylphosphine-mediated synthesis of 2-Acyl furans from ynenones

Xu, C., Wittmann, S., Gemander, M., Ruohonen, V. and Clark, J. S. (2017) Trialkylphosphine-mediated synthesis of 2-Acyl furans from ynenones. Organic Letters, 19(13), pp. 3556-3559. (doi: 10.1021/acs.orglett.7b01533) (PMID:28654294)

Abstract

A novel reaction for the synthesis of 2-acyl furans is reported. The reaction is believed to proceed by sequential addition of a trialkylphosphine to an ynenone, 5-exo-dig cyclization to form the furan, and oxidation of the resulting phosphonium ylide with molecular oxygen. Many common functional groups are tolerated during the reaction, and the products are obtained in good to excellent yield under the mild conditions. This methodology offers efficient access to biologically important compounds, including fused polycyclic compounds and furaldehydes, from simple starting materials.

• Item Type: Articles (Letter)
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Clark, Professor Stephen and Wittmann, Mr Stephane
• Authors: Xu, C., Wittmann, S., Gemander, M., Ruohonen, V., and Clark, J. S.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• Publisher: American Chemical Society
• ISSN: 1523-7060
• ISSN (Online): 1523-7052
• Published Online: 27 June 2017
• Copyright Holders: Copyright © 2017 American Chemical Society
• First Published: First published in Organic Letters 19(13):3556-3559
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher