Computational prediction of the enantioselectivity of a solid-state photoreaction

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1279-1281

  Garcia Garibay, Miguel A ^a   Houk, K N ^a   Keating, Amy E ^a   Cheer, Clair J ^b   Leibovitch, Mordechai ^b   Scheffer, John R ^b   Wu, Lian Chung ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001150986     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990952d     Document Type: Article

References (27)

1. (a) Keating, A. E.; Garcia-Garibay, M. A. In Molecular and Supramolecular Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Marcel Dekker: New York, 1998: Vol. 2, Chapter 5.
2. (b) Ito, Y. Synthesis 1998, 1.
3. (c) Sakamoto, M. Chem. Eur. J. 1997, 3, 684.
4. (d) Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; Chapter 5.
5. Cohen, M. D. Angew. Chem., Int. Ed. Engl. 1975, 14, 386.
6. Weiss, R. G.; Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530.
7. Warshel, A.; Shakked, Z. J. Am. Chem. Soc. 1975, 97, 5697.
8. (a) Bianchi, R.; Gavezzotti, A. Chem. Phys. Lett. 1986, 128, 295.
9. (b) Gavezzotti, A. Tetrahedron 1987, 43, 1241.
10. (a) Ariel, S.; Askari, S.; Scheffer, J. R.; Trotter, J.; Walsh, L. In Organic Phototransformations in Nonhomogeneous Media; Fox, M. A., Ed.; American Chemical Society: Washington, DC, 1985; pp 243-256.
11. (b) Ariel, S.; Askari, S.; Evans, S. V.; Hwang, C.; Jay, J.; Scheffer, J. R.; Trotter, J.; Walsh, L.; Wong, Y.-F. Tetrahedron 1987, 43, 1253.
12. Kearsley, S. K.; McBride, J. M. Mol. Cryst. Liq. Cryst. 1988, 156, 109.
13. (a) Zimmerman, H. E.; Zuraw, M. J. J. Am. Chem. Soc. 1989, 111, 2358.
14. (b) Zimmerman, H. E.; Zuraw, M. J. J. Am. Chem. Soc. 1989, 111, 7974.
15. (c) Zimmerman, H. E.; Zhu, Z. J. Am. Chem. Soc. 1994, 116, 9757.
16. (d) Zimmerman, H. E.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 5245.
17. (a) Keating, A. E.; Shin, S. H.; Houk, K. N.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1997, 119, 1474.
18. (b) Keating, A. E.; Shin, S. H.; Huang, F. K.; Garrell, R. L.; Garcia-Garibay, M. A. Tetrahedron Lett. 1999, 40, 261.
19. Wu, L.-C.; Cheer, C. J.; Olovsson, G.; Scheffer, J. R.; Trotter, J.; Wang, S.-L.; Liao, F.-L. Tetrahedron Lett. 1997, 38, 3135.
20. For a discussion of this phenomenon, see: Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Wiley: New York, 1981.
21. The first example of an absolute asymmetric synthesis was provided by Penzien, K.; Schmidt, G. M. Angew. Chem., Int. Ed. Engl. 1969, 8, 608. For later examples, see: Casell, L.; Garcia-Garibay, M. A.; Schefter, J. R.; Trotter, J. J. Chem. Educ. 1993, 70, 785 and references therein.
22. The first example of an absolute asymmetric synthesis was provided by Penzien, K.; Schmidt, G. M. Angew. Chem., Int. Ed. Engl. 1969, 8, 608. For later examples, see: Casell, L.; Garcia-Garibay, M. A.; Schefter, J. R.; Trotter, J. J. Chem. Educ. 1993, 70, 785 and references therein.
23. Sato, M.; Katagiri, N.; Makoto, M.; Haneda, T.; Kaneko, T. Tetrahedron Lett. 1986, 27, 6091.
24. Photoproduct 2 is a reasonable transition state analogue since it contains geometric changes similar to those that occur in the transition state (particularly ring bending), but to an exaggerated extent. This is desirable for the purposes or our calculations since we are looking for small energy differences at the limit of what is detectable with molecular mechanics.
25. (a) Mohammadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
26. (b) Weiner, S. J.; Kollman, P. A.; Nguyen, D. A. J. Comput. Chem. 1986, 7, 230; Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765.
27. (b) Weiner, S. J.; Kollman, P. A.; Nguyen, D. A. J. Comput. Chem. 1986, 7, 230; Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765.