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Note | Regular issue | Vol 55, No. 3, 2001, pp.569-577
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9143
Enantioselective Synthesis of 2- and 3-Benzofuryl β-Amino Alcohols

Marek Zaidlewicz,* Aldona Chechlowska, Andrzej Prewysz-Kwinto, and Andrzej Wojtczak

*Facutly of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland

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.