Predominant (S)-enantioselective inclusion of aryl methyl sulfoxides by (S)-isoleucyl-(S)-phenylglycines

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 660-665

  Akazome, Motohiro ^a   Doba, Ai ^a   Matsumoto, Shoji ^a   Ogura, Katsuyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHANNEL CAVITIES; CHIRAL RECOGNITION; DI-PEPTIDES; DIPEPTIDE; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; HOMOCHIRAL; HOST GUEST INTERACTIONS; HOST MOLECULES; HYDROGEN BONDINGS; INCLUSION COMPOUNDS; LAYER STRUCTURES; PHENYL GROUP; PHENYLGLYCINES; SCREW AXIS; SELF-ASSEMBLED; SELF-RECOGNITION; SINGLE CRYSTAL X-RAY ANALYSIS;

DRUG INTERACTIONS; ENANTIOSELECTIVITY; HYDROGEN BONDS; OXYGEN; STEREOCHEMISTRY;

CRYSTALLOGRAPHY;

ALANYLPHENYLGLYCINE DERIVATIVE; DIMETHYL SULFOXIDE; DIPEPTIDE; ISOLEUCYLPHENYLGLYCINE DERIVATIVE; LEUCYLPHENYLGLYCINE DERIVATIVE; METHYLPHENYL SULFOXIDE; METHYLTOLYL SULFOXIDE; METHYLXYLYL SULFOXIDE; OXYGEN; PHENYL GROUP; PHENYLGLYCINE; PROTON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGEN BOND; NONHUMAN; STEREOCHEMISTRY; X RAY ANALYSIS;

GLYCINE; HYDROGEN BONDING; ISOLEUCINE; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFOXIDES;

EID: 75749096918     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902197k     Document Type: Article

References (33)

1. (a) Pellissier, H. Tetrahedron 2006, 6, 5559-5601.
2. (b) Fernández, I; Khiar, N. Chem. Rev. 2003, 103, 3651-3705.
3. (c) Carreńo, M. C. Chem. Rev. 1995, 95, 1717-1760 and references therein.
4. (a) Andersen, K. K. Tetrahedron Lett. 1962, 3, 93-95.
5. (b) Andersen, K. K.; Gaffield, W.; Papanikolau, N. E.; Foley, J. W.; Perkins, R. I. J. Am. Chem. Soc. 1964, 86, 5637-5646.
6. Separations and Reactions in Organic Supramolecular Chemistry; Perspectives in Supramolecular Chemistry; Toda, F., Bishop, R., Eds.; John Wiley & Sons: West Sussex U.K., 2004; Vol. 8.
7. (a) Akazome, M.; Hirabayashi, A.; Senda, K.; Ogura, K. Tetrahedron 2007, 63, 9933-9938.
8. (b) Akazome, M.; Hirabayashi, A.; Takaoka, K.; Nomura, S.; Ogura, K. Tetrahedron 2005, 61, 1107-1113.
9. (c) Akazome, M.; Hirabayashi, A.; Ogura, K. Tetrahedron 2004, 60, 12085-12093.
10. (d) Akazome, M.; Ueno, Y.; Ooiso, H.; Ogura, K. J. Org. Chem. 2000, 65, 68-76.
11. (e) Akazome, M.; Noguchi, M.; Tanaka, O.; Sumikawa, A.; Uchida, T.; Ogura, K. Tetrahedron 1997, 53, 8315-8322.
12. (f) Ogura, K.; Uchida, T.; Noguchi, M.; Minoguchi, M.; Murata, A.; Fujita, M.; Ogata, K. Tetrahedron Lett. 1990, 31, 3331-3334.
13. (a) Toda, F.; Tanaka, K.; Okuda, T. J. Chem. Soc., Chem. Commun. 1995, 639-640.
14. (b) Weber, E.; Wimmer, C.; Liamas-Saiz, A. L.; Foces-Foces, C. J. Chem. Soc., Chem. Commun. 1992, 733-735.
15. (c) Toda, F.; Tanaka, K.; Nagamatsu, S. Tetrahedron Lett. 1984, 25, 4929-4932.
16. (d) Toda, F.; Tanaka, K.; Mak, T. C. W. Chem. Lett. 1984, 2085-2088.
17. In proteins, π-π interactions of their side chains have already been investigated to reveal the edge-to-face interaction between two benzene rings to be important: (a) Burley, S. K.; Petsko, G. A. Science 1985, 229, 23-28.
18. (b) Gould, R. O.; Gray, A. M.; Taylor, P.; Walkinshaw, M. D. J. Am. Chem. Soc. 1985, 107, 5921-5927.
19. (c) Burley, S. K.; Petsko, G. A. J. Am. Chem. Soc. 1986, 108, 7995-8001.
20. (a) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-668.
21. (b) Swift, J. A.; Pal, R.; McBride, J. M. J. Am. Chem. Soc. 1998, 120, 96-104.
22. (c) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029-12037.
23. (d) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
24. Akazome, M.; Matsuno, H.; Ogura, K. Tetrahedron: Asymmetry 1997, 8, 2331-2336.
25. Doyle, F. P.; Fosker, G. R.; Nayler, J. H. C.; Smith, H. J. Chem. Soc. 1962, 1440-1444.
26. Zervas, L; Winitz, M.; Greenstein, J. P. J. Org. Chem. 1957, 22, 1515-1521.
27. König, W.; Geiger, R. Chem. Ber. 1970, 103, 788-798.
28. Sandler, S. R.; Karo, W. Organic Functional Group Preparations, 2nd ed.; Academic Press, Inc.; San Diego, 1989; Vol. 1, Chapter 18, p 585.
29. Sandler, S. R.; Karo, W. Organic Functional Group Preparations, 2nd ed.; Academic Press, Inc.; San Diego, 1989; Vol. 1, Chapter 19, p 603.
30. Holland, H. L.; Pöpperl, H.; Ninniss, R. W.; Chenchaiah, P. C. Can. J. Chem. 1985, 63, 1118-1120.
31. Bordwell, F. G.; Boutan, P. J. J. Am. Chem. Soc. 1957, 79, 717-722.
32. Drabowicz, J.; Duddeck, H. Sulfur Lett. 1989, 10, 37-40.
33. Sheldrick, G. M. SHELXS-97 and SHELXL-97; University of Göttingen: Göttingen, Germany, 1997.