Organocatalytic synthesis of highly substituted furfuryl alcohols and amines

Clark, J.S. , Boyer, A. , Aimon, A., Garcia, P.E., Lindsay, D.M., Symington, A.D.F. and Danoy, Y. (2012) Organocatalytic synthesis of highly substituted furfuryl alcohols and amines. Angewandte Chemie (International Edition), 51(48), pp. 12128-12131. (doi: 10.1002/anie.201207300)

Abstract

A simple organocatalytic synthesis of substituted furans has been developed. The novel features of the procedure include the use of a simple thioether as the organocatalyst, the formation of a furan under neutral conditions rather than the anionic or acidic conditions employed in conventional syntheses, and the intermediacy of a versatile sulfonium ylide that has the potential to be intercepted directly by a variety of electrophiles rather than being protonated to give a sulfonium ion. The reaction proceeds with a wide range of substrates and nucleophiles to give highly decorated furans in good yield. The process is mild and can lead to the formation of a fragile, biologically-relevant epoxyfuran motif. The complementary nature of the thioether catalysis with other organocatalyzed processes has allowed the reaction to be incorporated into a three-component domino sequence.

• Item Type: Articles (Other)
• Keywords: Domino reactions, enynes, furans, organocatalysis, thioethers
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Lindsay, Dr David and Clark, Professor Stephen and Boyer, Dr Alistair
• Authors: Clark, J.S., Boyer, A., Aimon, A., Garcia, P.E., Lindsay, D.M., Symington, A.D.F., and Danoy, Y.
• Subjects: Q Science > QD Chemistry
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Angewandte Chemie (International Edition)
• Journal Abbr.: Angew Chem Int Ed Engl
• Publisher: Wiley - V C H Verlag GmbH & Co. KGaA
• ISSN: 1433-7851
• ISSN (Online): 1521-3773
• Published Online: 24 October 2012