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  • Reactions of Unsymmetric Chiral Dialdehydes with Lysine: Regio‐ and Enantioselective Macrocyclization and Fluorescent Sensing

This content will become publicly available on December 23, 2025

Title: Reactions of Unsymmetric Chiral Dialdehydes with Lysine: Regio‐ and Enantioselective Macrocyclization and Fluorescent Sensing
Abstract Three BINOL‐based unsymmetric chiral dialdehydes, (S)‐4, (S)‐5, and (S)‐6, each containing a salicylaldehyde moiety and anortho‐,meta‐ orpara‐substituted benzaldehyde unit, are synthesized and used to react with the enantiomers of an unsymmetric chiral diamine, lysine. These reactions represent the first examples of regioselective as well as enantioselective reactions of an unsymmetric chiral dialdehyde with an unsymmetric chiral diamine to generate unsymmetric chiral macrocycles. The addition of Zn2+can further enhance the selectivity for the macrocycle formation. Compounds (S)‐4and (S)‐5are found to exhibit chemoselective and enantioselective fluorescent recognition of lysine in the presence of Zn2+.  more » « less
Award ID(s):
2153466
PAR ID:
10565368
Author(s) / Creator(s):
 ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
European Journal of Organic Chemistry
Volume:
28
Issue:
8
ISSN:
1434-193X
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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