Synthesis of Enantiopure o-Hydroxybenzylamines by Stereoselective Reduction of 2-Imidoylphenols: Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes

European Journal of Organic ChemistryVolume 1999, Issue 4 p. 805-811 Full Paper Synthesis of Enantiopure o-Hydroxybenzylamines by Stereoselective Reduction of 2-Imidoylphenols: Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes Gianni Palmieri, Gianni Palmieri palmieri@camserv.unicam.it Search for more papers by this author Gianni Palmieri, Gianni Palmieri palmieri@camserv.unicam.it Search for more papers by this author First published: April 1999 https://doi.org/10.1002/(SICI)1099-0690(199904)1999:4<805::AID-EJOC805>3.0.CO;2-RCitations: 48AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract Enantiopure o-hydroxybenzylamines 2a–i were synthesized by diastereoselective reduction of the 2-imidoylphenols (R)-1a–i. Conformational analysis enabled the assignment of the absolute configurations of compounds 2a–i. The accessible o-hydroxybenzylamine (R,R)-2h serves as an effective catalyst precursor for highly enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes. This pathway represents a practical and operationally very simple methodology for the enantioselective synthesis of both the enantiomers of secondary alcohols 7a–f. Citing Literature Volume1999, Issue4April 1999Pages 805-811 RelatedInformation