Stereocomplexity and stereoselective synthesis of triamine molecules bearing four chiral carbon centers: Stereodifferentiated preparation of all 10 stereoisomers of 2,6-bis[1-(1-phenylethylamino)ethyl]pyridines.
Compounds (S,S)-2,6-bis(1-hydroxyethyl)pyridine, (R,R)-2,6-bis(1-acetoxyethyl)pyridine, and (1R,1'S)-2-(1-acetoxyethyl)-6-(1'-hydroxyethyl)pyridine were obtained by lipase-catalyzed kinetic acetylation of 2,6-bis(1-hydroxyethyl)pyridine as enantiomerically pure forms. The stereospecific replacement of hydroxy groups with (R)-phenylethylamine or (S)-phenylethylamine via its methanesulfonate or toluenesulfonate simultaneously or stepwise afforded all the stereoisomers of 1. Stereospecific preparation of all the 10 possible stereoisomers of 2,6-bis[1-(1-phenylethylamino)ethyl]pyridines 1a-f was achieved. Triamine 1b reacted with ZnCl2 to form Zn-triamine complex 16, the structure of which was determined by X-ray crystallographic analysis.
Uenishi
Jun'ichi
J
Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan. juenishi@mb.kyoto-phu.ac.jp
Aburatani
Sachiko
S
Takami
Taro
T
D000588:Amines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D011522:Protons; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000588:Amines; D011522:Protons; D011725:Pyridines; D002244:Carbon; D015032:Zinc