Rational design of CH/π interaction sites in a basic resolving agent

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7436-7441

  Kobayashi, Yuka ^a   Kurasawa, Toshie ^a   Kinbara, Kazushi ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

BASIC RESOLVING AGENTS; CHIRAL RECOGNITION;

AROMATIC COMPOUNDS;

1 AMINOBENZ[F]INDAN 2 OL; 1 AMINOINDAN 2 OL; ARYLALIPHATIC CARBOXYLIC ACID; ARYLBUTYRIC ACID DERIVATIVE; INDAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; MOLECULAR RECOGNITION; RACEMIC MIXTURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 6344280750     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049154d     Document Type: Article

References (19)

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13. Sujit, K.; Ghorai, K. S.; Harza, K. N.; Mal, D. Tetrahedron Lett. 1998, 39, 689.
14. We used (1R,2S)-1-aminobenz[f]indan-2-ol (ABI) and compared its chiral recognition ability with that of (1S,2R)-1-aminoindan-2-ol (AI); their absolute configurations are inverse to each other. Consequently, the less-soluble diastereomeric salts with ABI and AI consist of the amino alcohol and the antipodes of the arylalkanoic acids, respectively.
15. Cambridge Crystallographic Data Centre, ref CCDC-140008, contains the supplementary crystallographic data for (1S,2R)-1-amino-indan-2-ol-(R)-2-(3- methylphenyl)propionic acid (AI·1c) salt.1 These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html.
16. The less-soluble salts are ABI·(S)-1c and AI·(A)-1c.
17. Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2000, 122, 15, 3746.
18. We defined CH/π interactions as those with a C⋯π-plane distance less than 4.1 Å, according to the intermolecular interaction potentials of benzene-methane complexes estimated with ab initio molecular orbital calculations.10
19. The salt crystal contains single enantiomers of 2 and ABI. This means that the actually deposited crystals consist of ABI·(S)-2 and ABI·(R)-2 as the major and minor diastereomeric salts, respectively.