A new hydrogen-bonding motif for chiral recognition in the diastereomeric salts of racemic 1-phenylethylamine derivatives with enantiopure O-ethyl phenylphosphonothioic acid

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4227-4230

  Kobayashi, Yuka ^a   Morisawa, Fumi ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLBENZYLAMINE; AMINE;

ARTICLE; CHEMICAL INTERACTION; CHIRALITY; CRYSTALLIZATION; ENANTIOSELECTIVITY; HYDROGEN BOND; MOLECULAR RECOGNITION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 9444275944     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0483145     Document Type: Article

References (25)

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16. For details of the synthesis and enantioseparation of racemic O-ethyl phenylphosphonothioic acid, see Supporting Information. In a similar manner, several kinds of enantiopure O-substituted phosphonothioic acids could be prepared. The application of the phosphonothioic acids as resolving agents is now in progress.
17. The enantioseparations were carried out under almost the same conditions. The diastereomeric salt was crystallized from stirred ether/hexane at room temperature. The amount and ratio of the mixed solvent were adjusted to control the yield of the precipitated salt as close as possible within 50-80%.
18. 3 Z = 16, R = 0.0660, Rw = 0.0710. For preliminary data for the other crystals, see Supporting Information.
19. (a) Jaques, J.; Collet, A.; Wilen, S. H. In Enantiomers, Racemates and Resolution; Krieger Publishing Company: Malabor, FL, 1994.
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24. Very recently, the formation of a spherical cluster consisting of four carboxylic acid molecules and four amine molecules was reported. However, the carboxylic acid and amine are achiral; no chiral recognition phenomenon was observed. Sada, K.; Watanabe, T.; Miyamoto, J.; Fukuda, T.; Tohnami, N.; Miyata, M.; Kitayama, T.; Maehara, K.; Ute, K. Chem. Lett. 2004, 160-161.
25. Geometry optimizations were performed with B3LYP/3-21G* using the Gaussian 98 package. Frisch, M. J. et al. Gaussian 98, Revision A.11; Gaussian, Inc.: Pittsburgh, PA, 1998 [Full reference is given in Supporting Information]. For the initial coordinates of the more-soluble salt, the enantiomeric molecules of the amine component in the less-soluble salt crystal were replaced by the antipodes.