Synthesis, absolute configuration, and application of enantiopure trans-1-aminobenz[f]indan-2-ol.
Both novel enantiopure trans-1-aminobenz[f]indan-2-ols (4) were obtained from the racemate by the diastereomeric salt formation with (+)- and (-)-dibenzoyltartaric acids (8), respectively, and the absolute configuration of the enantiomer 4 in the less-soluble diastereomeric salt of racemic 4 with (+)-8 was determined to be (1S,2S) by an X-ray crystallographic analysis. The chiral recognition ability of the enantiopure amino alcohol was examined for the enantioseparation of racemic 2-arylalkanoic acids by the diastereomeric salt formation. The role of the naphthylene group of the amino alcohol was found to be closely associated with the stabilization of the crystal by CH/pi interactions on the basis of an X-ray crystallographic study.
Kobayashi
Yuka
Y
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
Kinbara
Kazushi
K
Sato
Masaaki
M
Saigo
Kazuhiko
K
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C514363:1-aminobenz(f)indan-2-ol; D000605:Amino Alcohols; D007189:Indans; D011083:Polycyclic Compounds; C093582:indan