Effects of magnesium salts and amines on the stereoselectivity in the imine aldol reaction.
In the imine aldol reactions of 1 with aromatic aldehydes using magnesium salts in the presence of amines, the threo/erythro ratios of products increased in the order Mg(ClO4)2>MgI2>MgBr2>MgCl2>Mg(OTf)2 and N,N,N',N'-tetramethylethylenediamine (TMEDA)>Et3N. This increase in the threo/erythro ratios of products was estimated to be caused by a retro-imine aldol reaction under thermodynamic control.
Hayashi
Kazuhiko
K
College of Pharmacy, Kinjo Gakuin University, 2-1723 Omori, Moriyama-ku, Nagoya 463-8521, Japan. hayashi@kinjo-u.ac.jp
Kujime
Eiko
E
Katayama
Hajime
H
Sano
Shigeki
S
Nagao
Yoshimitsu
Y
D000588:Amines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D017616:Magnesium Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011700:Putrescine / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013816:Thermodynamics
D000588:Amines; D007097:Imines; D007202:Indicators and Reagents; D017616:Magnesium Compounds; D011700:Putrescine