Crystal-to-crystal solid-state photochemistry: Absolute asymmetric β-thiolactam synthesis from an achiral α,β-unsaturated thioamide

Journal of the American Chemical Society

Volumn 118, Issue 43, 1996, Pages 10664-10665

  Sakamoto, Masami ^a   Takahashi, Masaki ^a   Kamiya, Kenji ^a   Yamaguchi, Kentaro ^a   Fujita, Tsutomu ^a   Watanabe, Shoji ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; THIOAMIDE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; TECHNIQUE; X RAY DIFFRACTION;

EID: 0029800115     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961878m     Document Type: Article

References (20)

1. Addadi, L.; Lahav, M. Origin of Optical Activity in Nature; Walker, D. C., Ed.; Elsevier: New York, 1979; Chapter 14.
2. Green, B. S.; Lahav, M.; Rabinovich, D. Acc. Chem. Res. 1979, 69, 191-197.
3. Scheffer, J. R.; Garcia-Garibay, M.; Nalamasu, O. Organic Photochemistry; Padwa, A., Ed., Marcel Dekker: New York and Basel, 1987; Vol. 8, pp 249-338.
4. Ramamurthy, V.; Weiss, R. G.; Hammond, G. S. Advances in Photochemistry; Volman, D. H., Hammond, G. S., Neckers, D. C., Ed.; John Wiley & Sons: New York, 1993; Vol. 18, pp 67-234.
5. Evans, S. V.; Garcia-Garibay, M.; Omkaram, N.; Scheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. Soc. 1986, 108, 5648-5649.
6. Roughton, A. L.; Muneer, M.; Demuth, M. J. Am. Chem. Soc. 1993, 115, 2085-2086.
7. Sekine, A.; Hori, K.; Ohashi, Y.; Yagi, M.; Toda, F. J. Am. Chem. Soc. 1989, 111, 697-680.
8. Sakamoto, M.; Hokari, N.; Takahashi, M.; Fujita, T.; Watanabe, S.; Iida, I.; Nishio, T. J. Am. Chem. Soc. 1993, 115, 818.
9. Sakamoto, M.; Takahashi, M.; Fujita, T.; Watanabe, S.; Iida, I.; Nishio, T. J. Org. Chem. 1995, 60, 3476-3477.
10. Sakamoto, M.; Takahashi, M.; Shimizu, M.; Fujita, T.; Nishio, T.; Iida, I.: Yamaguchi, K.; Watanabe, S. J. Org. Chem. 1995, 60, 7088-7089.
11. Sakamoto, M.; Takahashi, M.; Moriizumi, S.; Yamaguchi, K.; Fujita, T.; Watanabe, S. J. Am. Chem. Soc. 1996, 118, 8138-8139.
12. Garcia-Garibay, M.; Scheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. Soc. 1989, 111, 4985-4986.
13. Fu, T. Y.; Liu, Z.; Scheffer, J. R. J. Am. Chem. Soc. 1993, 115, 12202-12203.
14. Hashizume, D.; Kogo, H.; Sekine, A.; Ohashi, Y.; Miyamoto, H.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1996, 61-66.
15. We reported the solution photochemistry of the relevant N,N-dialkyl-α,β-unsaturated thioamides leading to the β-thiolactams and the debenzylated thioamides. Sakamoto, M.; Kimura, M.; Shimoto, T.; Fujita, T.; Watanabe, S. J. Chem. Soc., Chem. Commun. 1990, 1214-1215.
16. 3 at c 1.0.
17. Suzuki, T.; Fukushima, T.; Yamashita, Y.; Miyashi, T. J. Am. Chem. Soc. 1994, 116, 2793-2803.
18. w were 0.063 and 0.057.
19. w were 0.052 and 0.071.
20. The author has deposited atomic coordinates for both structures 1 and (R)-(+)-2 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB IEZ, UK.