title: Naphthyl groups in chiral recognition: structures of salts and esters of 2-methoxy-2-naphthylpropanoic acids.
abstract: The crystal structures of salt 8, which was prepared from (R)-2-methoxy-2-(2-naphthyl)propanoic acid ((R)-MβNP acid, (R)-2) and (R)-1-phenylethylamine ((R)-PEA, (R)-6), and salt 9, which was prepared from (R)-2-methoxy-2-(1-naphthyl)propanoic acid ((R)-MαNP acid, (R)-1) and (R)-1-(p-tolyl)ethylamine ((R)-TEA, (R)-7), were determined by X-ray crystallography. The MβNP and MαNP anions formed ion-pairs with the PEA and TEA cations, respectively, through a methoxy-group-assisted salt bridge and aromatic CH⋅⋅⋅π interactions. The networks of salt bridges formed 2(1)  columns in both salts. Finally, (S)-(2E,6E)-(1-(2) H(1) )farnesol ((S)-13) was prepared from the reaction of (2E,6E)-farnesal (11) with deuterated (R)-BINAL-H (i.e., (R)-BINAL-D). The enantiomeric excess of compound (S)-13 was determined by NMR analysis of (S)-MαNP ester 14. The solution-state structures of MαNP esters that were prepared from primary alcohols were also elucidated.
authors: Division of Insect Sciences, National Institute of Agrobiological Sciences, Tsukuba, Ibaraki 305-8634, Japan. ichikawa@affrc.go.jp
authors: Akio
authors: A
authors: Ichikawa
authors: Hiroshi
authors: H
authors: Ono
authors: Yuji
authors: Y
authors: Mikata
mesh_terms: D018360:Crystallography, X-Ray; D004952:Esters; D008968:Molecular Conformation; D011422:Propionates / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D011422:Propionates; D012492:Salts; C029658:propionic acid