Synthesis of Oxacyclic Scaffolds via Dual Ruthenium Hydride/Brønsted Acid??Catalyzed Isomerization/Cyclization of Allylic Ethers

…, R Petersen, MR Hansen, CL Hansen…

Index: Ascic, Erhad; Ohm, Ragnhild G.; Petersen, Rico; Hansen, Mette R.; Hansen, Casper L.; Madsen, Daniel; Tanner, David; Nielsen, Thomas E. Chemistry - A European Journal, 2014 , vol. 20, # 12 p. 3297 - 3300

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Citation Number: 15

Abstract

Abstract A ruthenium hydride/Brønsted acid-catalyzed tandem sequence is reported for the synthesis of 1, 3, 4, 9-tetrahydropyrano [3, 4-b] indoles (THPIs) and related oxacyclic scaffolds. The process was designed on the premise that readily available allylic ethers would undergo sequential isomerization, first to enol ethers (Ru catalysis), then to oxocarbenium ions (Brønsted acid catalysis) amenable to endo cyclization with tethered ...