A Gold-Catalyzed A3 Coupling/Cyclization/Elimination Sequence as Versatile Tool for the Synthesis of Furfuryl Alcohol Derivatives from Glyceraldehyde and Alkynes

摘要

The reaction of glyceraldehyde with alkynes delivers furfuryl alcohol derivatives within only one reaction step in the presence of a gold(III) catalyst. The reaction cascade is initiated by an intermolecular gold-catalyzed A3 coupling sequence in which morpholine is used as additive. Intramolecular cyclization and subsequent aromatization under elimination of the amine then deliver the target molecules. The protocol offers a valuable alternative to the common routes that are based on functionalization of already existing furan cores.