Enantiomeric recognition of alkyl phenyl sulfoxides by crystalline (R)-phenylglycyl-(R)-phenylglycine

Tetrahedron

Volumn 53, Issue 25, 1997, Pages 8315-8322

  Akazome, Motohiro ^a   Noguchi, Makoto ^a   Tanaka, Osamu ^a   Sumikawa, Atsuko ^a   Uchida, Tohru ^a   Ogura, Katsuyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030971016     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00522-X     Document Type: Article

References (14)

1. Molecular Inclusion and Molecular Recognition-Clathrates I and II, Topics in Current Chemistry; Weber, E., Ed.;. Springer-Verlag: Berlin-Heidelberg, 1987 and 1988; Vol. 140 and 149.
2. a) F. Toda, K. Tanaka, S. Nagamatsu, Tetrahedron Lett. 1984, 25, 4929.
3. b) F. Toda, K. Tanaka, T. C. W. Mak, Chem. Lett. 1984, 2085.
4. P. Charpin, E. Duñach, H. B. Kagan, F. R. Theobald, Tetrahedron Lett. 1986, 27, 2989.
5. A preliminary communication: K. Ogura, T. Uchida, M. Noguchi, M. Minoguchi, A. Murata, M. Fujita, K. Ogata, Tetrahedron Lett. 1990, 31, 3331.
6. Three types of interaction between two molecules of benzene ("tilted T", "T", and "parallel stacked and displaced" modes) must be taken into consideration. Jorgensen and Severance calculated these benzene diners by the Monte-Carlo method to show that they have comparable energies: W. L. Jorgensen, D. L. Severance, J. Am. Chem. Soc. 1990, 112, 4768.
7. The distance and angle of S=O⋯H-N hydrogen bonding: O⋯N 2.748(5) Å, O⋯H 1.98 Å, O⋯H-N 160.6° for the inclusion compound of (S)-2a; O⋯N 2.743(4) Å, O⋯H 1.81 Aring;, O⋯H-N 167.4° for the inclusion compound of (S)-2b; O⋯N 2.782(7) A, O⋯H 1.84 Aring;, O⋯H-N 165.8° for the inclusion compound of (R,R)-3. These values are almost same to the reported distances: 2.758(2) and 2.781(1) Aring; for SO⋯O of binaphthol;3 2.85(2) A⋯ for SO(sulfinyl)⋯N(amide).4
8. In proteins, π-π interactions on their side chains have already been investigated to reveal the edge-to-face interaction between two benzene rings to be important: (a) S. K. Burley, G. A. Petsko, Science 1985, 229, 23.
9. (b) R. O. Gould, A. M. Gray, P. Taylor, M. D. Walkinshaw, J. Am. Chem. Soc. 1985, 707, 5921.
10. S. K. Burley, G. A. Petsko, J. Am. Chem. Soc. 1986, 108, 7995.
11. For a review of CH/π interaction: M Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665 and references therein.
12. D. A. Dougherty, Science 1996, 271, 163.
13. When the resulting solution was allowed to stand for a long time, (R,R)-1 precipitated as crystals.
14. Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.