B(C6F5)3-catalyzed Prins/Ritter reaction: a novel synthesis of hexahydro-1H-furo[3,4-c]pyranyl amide derivatives

Abstract

The coupling of aldehydes or ketones with (2-(4-methoxyphenyl)-4-methylenetetrahydrofuran-3-yl)methanol in the presence of nitriles under the influence of 5mol% tris(pentaflourophenyl)borane at room temperature afforded a novel series of cis-fused hexahydro-1H-furo[3,4-c]pyran derivatives in good yields with high selectivity. This is the first report on the synthesis of hexahydro-1H-furo[3,4-c]pyranyl amide through a sequential Prins/Ritter reactions using B(C6F5)3 as a mild Lewis acid.