Stereoselectivity in Reactions of Metal Complexes. Part XVII. Synthesis of three new optically active triamines: 2,6-Bis{[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl}pyridine, 2,6-bis{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl}pyridine, and 2,6-bis{{(2S)-2-[(benzyloxy)methyl]pyrrolidin-1-yl}methyl}pyridine. X-ray structure and equilibrium behaviour of their copper(II) complexes

✍ Scribed by Klaus Bernauer; Thierry Chuard; Helen Stoeckli-Evans

• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: German
• Weight: 697 KB
• Volume: 76
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19930760611

✦ Synopsis

Abstract

The three new optically active triamines derived from 2,6‐bis(aminomethyl)pyridine, i.e. 2,6‐bis{[(2__S__)‐2‐(hydroxymethyl)pyrrolidin‐1‐yl]methyl}pyridine (3a), 2,6‐bis{[(2__S__)‐2‐(methoxymethyl)pyrrolidin‐1‐yl]methyl}‐pyridine (3b), and 2,6‐bis{{(2__S__)‐2‐[(benzyloxy)methyl]pyrrolidin‐1‐yl}methyl}pyridine (3c), were synthesized. The equilibrium behaviour in solution and Cu^II^ complex formation were studied by acidimetric titration and by UV/VIS and CD measurements. It was found that in aqueous solution, 3a can coordinate one of the CH~2~OH groups to Cu^II^ upon deprotonation. X‐Ray crystal structures were determined for the complexes [Cu(3a)Cl]ClO~4~·H~2~O, [Cu(3b)Cl]ClO~4~, and [Cu(3c)Cl]ClO~4~. In the solid state, coordination of both the OH and the alkoxy groups was observed, and the three ligands are pentacoordinated.