Stereoselective synthesis of α-aryl-2-benzofuranmethanamines and α-aryl-1H-indole-2-methanamines through palladium-mediated annulation of chiral α-arylpropargylamines

The title compds., valuable chiral synthons for the synthesis of biol. active compds., were prepd. in good yield and with high stereoselectivity through palladium-catalyzed heteroannulation of 2-iodophenol or N-(2-iodophenyl)methanesulfonamide with enantiomerically pure or enriched α-arylpropargylamines. For example, the annulation of (αS)-α-ethynylbenzenemethanamine with iodophenol gave (-)-(αR)-α-phenyl-2-benzofuranmethanamine. The annulation of (αS)-α-ethynylbenzenemethanamine with N-(2-iodophenyl)methanesulfonamide gave (-)-(αR)-1-(methylsulfonyl)-α-phenyl-1H-indole-2-methanamine.