Unprecedented InCl3-catalyzed formation of cis-fused perhydrofuro[2,3-b]oxepines

2-Methylindole and its N-substituted derivatives react smoothly with 2,3-dihydrofuran (DHF) in the presence of a catalytic amount of InCl3 under mild conditions to afford the corresponding 2-methyl-3-perhydrofuro[2,3-b]oxepin-4-yl-1H-indole derivatives in fairly good yields with high diastereoselectivity, while 3,4-dihydro-2H-pyran (DHP) affords exclusively 5,5-di(1H-3-indolyl)-1-pentanol derivatives in high yields under similar reaction conditions.