A NEW TWISTED DUAL HYDROGEN-BOND ACCEPTOR FEATURING AMIDINE FUNCTIONALITY FOR CHIRAL RECOGNITION - A HIGH-LEVEL OF ENANTIOSELECTION OF DIOLDERIVATIVES

Authors
DOBASHI Y KOBAYASHI K DOBASHI A
Citation
Y. Dobashi et al., A NEW TWISTED DUAL HYDROGEN-BOND ACCEPTOR FEATURING AMIDINE FUNCTIONALITY FOR CHIRAL RECOGNITION - A HIGH-LEVEL OF ENANTIOSELECTION OF DIOLDERIVATIVES, Tetrahedron letters, 39(1-2), 1998, pp. 93-96
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
1-2
Year of publication
1998
Pages
93 - 96
Database
ISI
SICI code
0040-4039(1998)39:1-2<93:ANTDHA>2.0.ZU;2-4
Abstract
The C-2 amidine derivative (S,S)-1, as a twisted chiral dual acceptor for hydrogen bonding, was designed and synthesized. Enantioselective b inding between (S,S)-1 and a series of diol enantiomers was investigat ed by NMR spectroscopy. High enantioselection above 1.0 kcal/mol was a chieved in CDCl3. The association mode based on dual N ... HO interact ions was confirmed by intermolecular NOEs. (C) 1997 Elsevier Science L td. All rights reserved.