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/...

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Veröffentlicht in:	Chemical & Pharmaceutical Bulletin 2007/12/01, Vol.55(12), pp.1773-1775
Hauptverfasser:	Hayashi, Kazuhiko, Kujime, Eiko, Katayama, Hajime, Sano, Shigeki, Nagao, Yoshimitsu
Format:	Artikel
Sprache:	eng
Schlagworte:	Amines - chemistry imine aldol reaction Imines - chemistry Indicators and Reagents magnesium Magnesium Compounds - chemistry Magnetic Resonance Spectroscopy Putrescine - chemistry retro-imine aldol reaction reverse stereoselectivity Spectrophotometry, Infrared Stereoisomerism thermodynamic control Thermodynamics
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Beschreibung
Zusammenfassung:	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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.55.1773