Synthesis, absolute configuration, and application of enantiopure trans-1-aminobenz[f]indan-2-ol.

Abstract:

: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.

journal_name

Chirality

journal_title

Chirality

authors

Kobayashi Y,Kinbara K,Sato M,Saigo K

doi

10.1002/chir.20101

subject

Has Abstract

pub_date

2005-02-01 00:00:00

pages

108-12

issue

2

eissn

0899-0042

issn

1520-636X

journal_volume

17

pub_type

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