Enantioselective synthesis of 2-and 3-benzofuryl beta-amino alcohols

Authors
Zaidlewicz, M Chechlowska, A Prewysz-Kwinto, A Wojtczak, A
Citation
M. Zaidlewicz et al., Enantioselective synthesis of 2-and 3-benzofuryl beta-amino alcohols, HETEROCYCLE, 55(3), 2001, pp. 569-577
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
3
Year of publication
2001
Pages
569 - 577
Database
ISI
SICI code
0385-5414(20010301)55:3<569:ESO23B>2.0.ZU;2-U
Abstract
Enantioselective reduction of 2- and 3-bromoacetylbenzofurans with (-)-B-ch lorodiisopinocampheylborane produced the corresponding bromohydrins which w ere transformed into (S)-(benzofuran-2-yl)oxirane of 70% ee and (S)-(benzof uran-3-yl)oxirane of 71% ee, respectively. The epoxides treated with primar y alkylamines gave the corresponding (S)-1-(benzofuran-2- and -3-yl)-2-(alk ylamino)ethanols.