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

Chirality

Volumn 17, Issue 2, 2005, Pages 108-112

  Kobayashi, Yuka ^a   Kinbara, Kazushi ^a   Sato, Masaaki ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

2 arylalkanoic acid; Crystal engineering; Diastereomeric salt; Enantiopure amino alcohol; Enantioseparation

Indexed keywords

1 AMINOBENZ[F]INDAN-2-OL; AMINOALCOHOL; ARYLALIPHATIC CARBOXYLIC ACID; DIBENZOYLTARTARIC ACID; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

AMINO ALCOHOLS; CRYSTALLOGRAPHY, X-RAY; INDANS; MOLECULAR CONFORMATION; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 13244292228     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20101     Document Type: Article

References (21)

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13. 3) δ 3.14 (d, J=16.6 Hz, 1H), 3.37 (d, J=18.0 Hz, 1H), 4.21 (t, J=2.7 Hz, 1H), 4.41 (d, J= 2.7 Hz, 1H), 7.26-7.95 (m, 6H).
14. 3) δ 2.13 (d, J=4.8 Hz, 1H), 3.37 (dd, J=6.3 Hz, J′=17.6 Hz, 1H), 3.45 (dd, J=6.3 Hz, J′-16.1 Hz, 1H), 4.55 (m, 1H), 4.84 (d, J=5.4 Hz, 1H), 7.40-7.83 (m, 6H).
15. 3) δ 1.68 (bs, 3H), 2.97 (dd, J= 8.4 Hz, J′=15.5 Hz, 1H), 3.36 (dd, J=6.6 Hz, J′=15.5 Hz, 1H), 5.00 (m, 2H), 7.40-7.83 (m, 6H).
16. w = 0.052, CCDC 248594 contains the supplementary crystallographic data for this article. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc. cam.ac.uk).
17. 1NMR were the same as those of (1S,2S)-4.
18. w = 0.050, CCDC 248595 contains the supplementary crystallographic data for this article. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).
19. (a) Kinbara K, Kobayashi Y, Saigo K. Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network. J Chem Soc Perkin Trans 2 2000:111-120.
20. (b) Kinbara K, Oishi K, Harada Y, Saigo K. Effect of a substituent on an aromatic group in diastereomeric resolution. Tetrahedron 2000;56:6651-6655.
21. (c) Kinbara K, Sakai K, Hashimoto Y, Nohira H, Saigo K. Chiral discrimination upon crystallization of the diastereomeric salts of 1-arylethylamines with mandelic acid or p-methoxymandelic acid: interpretation of the resolution efficiencies on the basis of the crystal structures. J Chem Soc Perkin Trans 2 1996;2615-2622.