ChemInform Abstract: Synthesis of Cyclopropyl‐Substituted Furans by Broensted Acid Promoted Cascade Reactions.

Abstract

Synthesis of Cyclopropyl-Substituted Furans by Broensted Acid Promoted CascadeReactions. -A high-yielding, diastereoselective intramolecular reaction cascade reaction is developed creating three new bonds in a single step, thus providing 2,3,5-substituted furans bearing a ring fused cyclopropyl substituent. Due to the instability of some of the required ynenone substrates an in-situ-preparation of the latter starting from 2-alkynals and acetylacetone is examined. The reaction is extended to a substrate bearing a pendant alkyne which cyclices to form a tricyclic acetal structure. -(CLARK*, J. S.; ROMITI, F.; HOGG, K. F.; HAMID, M. H. S. A.; RICHTER, S. C.; BOYER, A.; REDMAN, J. C.; FARRUGIA, L. J.; Angew. Chem., Int. Ed. 54 (2015) 19, 5744-5747, http://dx.doi.org/10.1002/anie.201500625 ; WestCHEM, Sch.