J. Clark, Alistair Boyer, A. Aimon
Nov 26, 2012
Citations
0
Influential Citations
47
Citations
Journal
Angewandte Chemie
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.