TY - JOUR AU - Gung, Benjamin W.; Conyers, Ryan C.; Wonser, Josh TI - Gold(I)-Catalyzed Intramolecular [4+3]-Cycloaddition Reactions with Furan Propargyl Esters as the Substrates: Carbenoid vs. Stabilized Allyl Cation SN - 0936-5214 SN - 1437-2096 PY - 2013 JO - Synlett JF - Synlett LA - EN VL - 24 IS - 10 SP - 1238 EP - 1242 ET - 2013/05/28 DA - 2013/06/05 KW - gold-catalyzed KW - cycloadditions KW - furan KW - propargyl ester KW - carbenoid AB - The tricyclic ring system with an oxabicyclo[3.2.1]octadiene and a fused six-membered ring was produced efficiently using the readily available propargyl ester furan substrate in the presence of a Au(I) complex. The reaction involves a tandem 3,3-rearrangement of the propargyl ester followed by an intramolecular [4+3]-cycloaddition reaction. Both the primary ligand of the gold complex (N-heterocyclic carbene; NHC) and a neutral dynamic ligand (PhCN) are important for the success of the reaction. PB - © Georg Thieme Verlag DO - 10.1055/s-0033-1338946 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0033-1338946 ER -