Asymmetric induction in photochemical reactions conducted in zeolites and in the crystalline state

Journal of the American Chemical Society

Volumn 118, Issue 5, 1996, Pages 1219-1220

  Leibovitch, Mordechai ^b   Olovsson, Gunnar ^b   Sundarababu, Gajendran ^a   Ramamurthy, V ^a   Scheffer, John R ^b   Trotter, James ^b  

^a Tulane University   (United States)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029918402     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953238+     Document Type: Article

References (20)

1. Inoue, Y. Chem. Rev. 1992, 92, 741.
2. For reviews on photochemistry in zeolites, see: (a) Ramamurthy, V. In Photochemisiry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991: Chapter 10. (b) Ramamurthy, V.; Eaton, D. F.; Caspar, J. V. Acc. Chem. Res. 1992, 25, 299.
3. For reviews on photochemistry in zeolites, see: (a) Ramamurthy, V. In Photochemisiry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991: Chapter 10. (b) Ramamurthy, V.; Eaton, D. F.; Caspar, J. V. Acc. Chem. Res. 1992, 25, 299.
4. Gudmundsdottir, A. D.; Scheffer, J. R.; Trotter, J. Tetrahedron Lett. 1994, 35, 1397 and references therein.
5. Reviews: Wagner, P.; Park, B.-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, Chapter 4. Wagner, P. J. Acc. Chem. Res. 1989, 22, 83.
6. Reviews: Wagner, P.; Park, B.-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, Chapter 4. Wagner, P. J. Acc. Chem. Res. 1989, 22, 83.
7. Lewis, F. D.; Johnson, R. W.; Johnson, D. E. J. Am. Chem. Soc. 1974, 96, 6090.
8. 5 was assigned on the basis of an X-ray crystal structure of the p-methoxy derivative carried out at UBC (Olovsson, G.; Trotter, J., unpublished results). The absolute configuration of the photoproducts has not been assigned. The possibility that what we took to be the minor enantiomer of photoproduct 2d on HPLC was an unidentified impurity was ruled out by (1) showing that this peak had exactly the same retention time as in the case of the racemic mixture, (2) checking the UV absorption spectrum of each peak (diode array detector), and (3) checking the enantiomeric excesses on two different HPLC columns (Chiralcel OD and OJ). Attempted determination of the enantiomeric excesses by chiral shift reagent NMR techniques was unsuccessful.
9. (a) Breck, D. W. Zeolite Molecular Sieves: Structure, Chemistry, and Use; Wiley: New York, 1974.
10. (b) van Bekkum, H.; Flanigen, E. M.; Jansen, J. C. Introduction to Zeolite Science and Practice: Elsevier: Amsterdam, 1991.
11. (c) Dyer, A. An Introduction to Zeolite Molecular Sieves; Wiley: Chichester, 1988.
12. Photolyses were also carried out on samples in which the order of inclusion was reversed, i.e., inclusion of ketone followed by inclusion of chiral inductor, as well as on samples prepared by simultaneous adsorption of ketone and chiral inductor from hexane solution. In both instances, the enantiomeric excesses obtained were considerably lower than those reported in Table 1.
13. For a description of the solid state photolysis procedure, see ref 3.
14. (a) Toda, F. Topics Curr. Chem. 1988, 149, 211.
15. (b) Toda, F. Mol. Cryst. Liq. Cryst. 1990, 41, 187.
16. (c) Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; Chapter 7.
17. (a) Green, B. S.; Lahav, M.; Rabinovich, D. Acc. Chem. Res. 1979, 12, 191.
18. (b) Vaida, M.; Popovitz-Biro, R.; Leiserowitz, L.; Lahav, M. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; Chapter 6.
19. (c) Scheffer, J. R.; Garcia-Garibay, M. In Photochemistry on Solid Surfaces; Anpo, M., Matsuura, T., Eds.; Elsevier: New York, 1989; Chapter 9.3.
20. (d) Caswell, L.; Garcia-Garibay, M. A.; Scheffer, J. R.; Trotter, J. J. Chem. Educ. 1993, 70, 785.