Solid state photochemical reaction of achiral N-(β,γ-unsaturated carbonyl)thiocarbamate to optically active thiolactone in the chiral crystalline environment

Chemical Communications

Volumn , Issue 21, 1998, Pages 2315-2316

  Sakamoto, Masami ^a   Takahashi, Masaki ^a   Arai, Takeshi ^a   Shimizu, Motoki ^a   Yamaguchi, Kentaro ^a   Mino, Takashi ^a   Watanabe, Shoji ^a   Fujita, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012469212     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805520c     Document Type: Article

References (13)

1. J. R. Scheffer, M. Garcia-Garibay and O. Nalamasu, Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, Basel, 1987, vol. 8, pp 249-338.
2. J. R. Scheffer and P. R. Pokkuluri, Photochemistry in Organized and Constrained Media, ed. V. Ramamurthy, VCH, New York, 1991, pp. 185-246.
3. K. Venkatesan and V. Ramamurthy, Photochemistry in Organized and Constrained Media, ed. V. Ramamurthy, VCH, New York, 1991, pp. 133-184.
4. V. Ramamurthy and K. Venkatesan, Chem. Rev., 1987, 87, 433.
5. Y. Ito, Synthesis, 1998, 1.
6. M. Sakamoto, N. Hokari, M. Takahashi, T. Fujita, S. Watanabe, I. Iida and T. Nishio, J. Am. Chem. Soc., 1993, 115, 818.
7. L. Addadi and M. Lahav, Origin of Optical Activity in Nature, ed. D. C. Walker, Elsevier, New York, 1979; ch. 14.
8. B. S. Green, M. Lahav and D. Rabinovich, Acc. Chem. Res., 1979, 69, 191.
9. F. Toda and S. Soda, J. Chem. Soc., Chem. Commun., 1987, 1413.
10. M. Vaida, R. Popovitz-Biro, L. Leiserowitz and M. Lahav, Photochemistry in Organized and Constrained Media, ed. V. Ramamurthy, VCH, New York, 1991, pp. 248-302.
11. M. Sakamoto, Chem. Eur. J., 1997, 3, 684.
12. 2 are torsion angles S1-C1-N1-C9 and O2-C1-N1-C3 , respectively, for τ of C(=S)-N. Twist angle τ for C(=O)-N is determined in the same manner.
13. M. Sakamoto, K. Obara, T. Fujita, S. Watanabe, T. Nishio and I. Iida, J. Org. Chem., 1992, 57, 3735.