Enantioselective Synthesis of 2- and 3-Benzofuryl b-Amino Alcohols

Abstract

Enantioselective reduction of 2-and 3-bromoacetylbenzofurans with (-)-B-chlorodiisopinocampheylborane produced the corresponding bromohydrins which were transformed into (S)-(benzofuran-2-yl)oxirane of 72% ee and (S)-(benzofuran-3-yl)oxirane of 71% ee, respectively.The epoxides treated with primary alkylamines gave the corresponding (S)-1-(benzofuran-2-and -3-yl)-2-(alkylamino)ethanols.