MalphaNP acid, a powerful chiral molecular tool for preparation of enantiopure alcohols by resolution and determination of their absolute configurations by the (1)H NMR anisotropy method.
A novel methodology using a chiral molecular tool of MalphaNP acid (1), 2-methoxy-2-(1-naphthyl)propionic acid, useful for preparation of enantiopure secondary alcohols and determination of their absolute configurations by the (1)H NMR anisotropy method was developed; racemic MalphaNP acid (1) was enantioresolved with (-)-menthol, and the enantiopure MalphaNP acid (S)-(+)-(1) obtained was allowed to react with racemic alcohol, yielding a mixture of diastereomeric esters, which was clearly separated by HPLC on silica gel. By applying the sector rule of (1)H NMR anisotropy effect, the absolute configuration of the first-eluted MalphaNP ester was unambiguously determined. Solvolysis or reduction of the first-eluted MalphaNP esters yielded enantiopure alcohols.
Kasai
Yusuke
Y
Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Aoba, Sendai, Japan.
Taji
Hiromi
H
Fujita
Takuma
T
Yamamoto
Yoko
Y
Akagi
Megumi
M
Sugio
Akinori
A
Kuwahara
Shunsuke
S
Watanabe
Masataka
M
Harada
Nobuyuki
N
Ichikawa
Akio
A
Schurig
Volker
V
D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification*; D016880:Anisotropy; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry*; D058428:Silica Gel; D012822:Silicon Dioxide; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds
D000438:Alcohols; D007202:Indicators and Reagents; D009281:Naphthalenes; D011422:Propionates; D013438:Sulfhydryl Compounds; C499260:2-methoxy-2-(1-naphthyl)propionic acid; D058428:Silica Gel; D012822:Silicon Dioxide