title: 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.
abstract: 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.
authors.affiliation: Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Aoba, Sendai, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kasai
authors.forename: Hiromi
authors.initials: H
authors.lastname: Taji
authors.forename: Takuma
authors.initials: T
authors.lastname: Fujita
authors.forename: Yoko
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Megumi
authors.initials: M
authors.lastname: Akagi
authors.forename: Akinori
authors.initials: A
authors.lastname: Sugio
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Kuwahara
authors.forename: Masataka
authors.initials: M
authors.lastname: Watanabe
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Harada
authors.forename: Akio
authors.initials: A
authors.lastname: Ichikawa
authors.forename: Volker
authors.initials: V
authors.lastname: Schurig
mesh_terms: 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
chemical_list: 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