New method for the synthesis of alpha-substituted tetrahydrofuran-2-methanols through diastereoselective addition of THF to aldehydes mediated by Et3B in the presence of air

Authors
Yoshimitsu, T Tsunoda, M Nagaoka, H
Citation
T. Yoshimitsu et al., New method for the synthesis of alpha-substituted tetrahydrofuran-2-methanols through diastereoselective addition of THF to aldehydes mediated by Et3B in the presence of air, CHEM COMMUN, (17), 1999, pp. 1745-1746
Citations number
33
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
17
Year of publication
1999
Pages
1745 - 1746
Database
ISI
SICI code
1359-7345(19990907):17<1745:NMFTSO>2.0.ZU;2-9
Abstract
The tetrahydrofuranyl radical, generated from THF with Et3B in the presence of air, was found to react with aldehydes threo-selectively to afford alph a-substituted tetrahydrofuran-2-methanols, the common structural motifs of biologically active acetogenin polyketides, in moderate yields.