Light-induced transfer of molecular chirality in solution: Enantiospecific photocyclization of molecularly chiral acrylanilides

Journal of the American Chemical Society

Volumn 131, Issue 14, 2009, Pages 5036-5037

  Ayitou, Anoklase Jean Luc ^a   Sivaguru, J ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AXIAL CHIRALITY; ENANTIOSPECIFIC; HIGH ENANTIOSELECTIVITY; MOLECULAR CHIRALITY; PHOTOCYCLIZATION; PHOTOPRODUCT; ZWITTERIONIC INTERMEDIATE;

CHIRALITY; ENANTIOSELECTIVITY; OLEFINS; STEREOCHEMISTRY;

ENANTIOMERS;

ANILIDE; O TERT BUTYLACRYLANILIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONTROLLED STUDY; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGHT; MOLECULAR MECHANICS; PHOTOREACTIVITY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 67849128985     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9003552     Document Type: Article

References (31)

1. Inoue, Y. In Chiral Photochemistry; Inoue, Y., Ramamurthy, V., Eds.; Marcel Dekker: New York, 2004; Vol. 11, p 129.
2. Turro, N. J.; Garcia-Garibay, M. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; Wiley-VCH: New York, 1991, p 1.
3. (a) Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Wiley-VCH: New York, 1991, p 429.
4. (b) Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647.
5. (c) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203.
6. (d) Mori, T.; Weiss, R. G.; Inoue, Y. J. Am. Chem. Soc. 2004, 126, 8961.
7. (e) Bauer, A.; Westkämper, F.; Grimme, S.; Bach, T. Nature 2005, 436, 1139.
8. (f) Bach, T.; Bergmann, H.; Grosch, B.; Harms, K. J. Am. Chem. Soc. 2002, 124, 7982.
9. Sakamoto, M.; Iwamoto, T.; Nono, N.; Ando, M.; Arai, W.; Mino, T.; Fujita, T. J. Org. Chem. 2003, 68, 942.
10. In spite of the lack of chirality in the individual molecules/units, the crystals could be chiral. These are labeled as molecular chiral crystalline compounds (see refs 3c and 4).
11. (a) Dunitz, J. D. Chem. Commun. 2003, 545.
12. (b) Curtin, D. Y.; Paul, I. C. Chem. Rev. 1981, 81, 525.
13. (a) Toda, F. Acc. Chem. Res. 1995, 28, 480.
14. (b) Sakamoto, M.; Kato, M.; Aida, Y.; Fujita, K.; Mino, T.; Fujita, T. J. Am. Chem. Soc. 2008, 130, 1132.
15. (c) Veerman, M.; Resendiz, M. J. E.; Garcia-Garibay, M. A. Org. Lett. 2006, 8, 2615.
16. (a) Bach, T.; Schröder, J.; Harms, K. Tetrahedron Lett. 1999, 40, 9003.
17. (b) Muller, C.; Bach, T. Aust. J. Chem. 2008, 61, 557.
18. (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131.
19. (b) Clayden, J. Chem. Commun. 2004, 127.
20. (c) Honda, A.; Waltz, K. M.; Carroll, P. J.; Walsh, P. J. Chirality 2003, 15, 615.
21. Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B. l.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955.
22. (a) Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586.
23. (b) Ates, A.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130.
24. (a) Ogata, Y.; Takagi, K.; Ishino, I. J. Org. Chem. 1971, 36, 3975.
25. (b) Bach, T.; Grosch, B.; Strassner, T.; Herdtweck, E. J. Org. Chem. 2003, 68, 1107.
26. (c) Toda, F.; Miyamoto, H.; Kanemoto, K. J. Org. Chem. 1996, 61, 6490.
27. (d) Tanaka, K.; Kakinoki, O.; Toda, F. Chem. Commun. 1992, 1053.
28. Ayitou, J.-L. A.; Ugrinov, A.; Sivaguru, J. Photochem. Photobiol. Sci. 2009, DOI: 10.1039/B903861B.
29. Naito, T.; Tada, Y.; Ninomiya, I. Heterocycles 1984, 22, 237.
30. See the Supporting Information.
31. Havinga, E.; Schlatmann, J. L. M. A. Tetrahedron 1961, 16, 146.