CHIRAL RECOGNITION OF 1,1'-BI-2-NAPHTHOL ENANTIOMERS BY TWISTED AMIDINE DERIVATIVES - RATIONAL DESIGN OF A HIGHLY ENANTIOSELECTIVE RECEPTOR

Authors
DOBASHI Y KOBAYASHI K SATO N DOBASHI A
Citation
Y. Dobashi et al., CHIRAL RECOGNITION OF 1,1'-BI-2-NAPHTHOL ENANTIOMERS BY TWISTED AMIDINE DERIVATIVES - RATIONAL DESIGN OF A HIGHLY ENANTIOSELECTIVE RECEPTOR, Tetrahedron letters, 39(19), 1998, pp. 2985-2988
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
19
Year of publication
1998
Pages
2985 - 2988
Database
ISI
SICI code
0040-4039(1998)39:19<2985:CRO1EB>2.0.ZU;2-7
Abstract
Clarification of the molecular structures of diastereomeric complexes relevant to the enantioselective dual N ... HO bonding between the chi ral C-2 amidine derivative (S,S)-1 and 1,1'-bi-2 naphthol 2 in CDCl3 a fforded the structural factor determining the sense of observed enanti oselection. This insight into chiral recognition was successfully appl ied to the design of a new twisted dual hydrogen bond acceptor (S,S)-3 that exhibited a higher level of enantioselectivity toward 2. (C) 199 8 Elsevier Science Ltd. All rights reserved.