67246-76-8Relevant academic research and scientific papers
Naphthyl groups in chiral recognition: Structures of salts and esters of 2-methoxy-2-naphthylpropanoic acids
Ichikawa, Akio,Ono, Hiroshi,Mikata, Yuji
, p. 2294 - 2304,11 (2012)
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 21 columns in both salts. Finally, (S)-(2E,6E)-(1-2H 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. Princess and the PEA: The crystal structures of the MαNP and MβNP salts were determined by X-ray crystallography. The 1-naphthyl group of the MαNP anion and the 2-naphthyl group of the MβNP anion acted as a C-H donor and -acceptor, respectively. Copyright
