A comparison between zeolites and crystalline state as reaction media: Asymmetric induction during photocyclization of α-mesitylacetophenones to 2-indanols

Molecular Crystals and Liquid Crystals

Volumn 456, Issue 1, 2006, Pages 71-84

  Natarajan, Arunkumar ^a,c   Ramamurthy, V ^a   Mague, Joel T ^b  

^a University of Miami   (United States)

^b Tulane University   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

hydrogen abstraction; Chiral induction; Crystalline state; Diastereoselectivity; Mesitylacetophenones; Photocyclization; Zeolites

Indexed keywords

CRYSTALLINE STATE; MESITYLACETOPHENONES; PHOTOCYCLIZATION; REACTION MEDIA;

ALCOHOLS; CRYSTAL STRUCTURE; CRYSTALLINE MATERIALS; ISOMERIZATION; KETONES; REACTION KINETICS;

ZEOLITES;

EID: 33751509656     PISSN: 15421406     EISSN: 15635287     Source Type: Journal    
DOI: 10.1080/15421400600786355     Document Type: Conference Paper

References (25)

1. Inoue, Y. & Ramamurthy, V. (Eds.), (2004), Chiral Photochemistry, Marcell Dekker; New York, Vol. 11, 129.
2. a) Rau, H. (2004). In: Chiral Photochemistry, Inoue, Y. & Ramamurthy, V. (Eds.), Marcel Dekker; New York;
3. b) Hammond, G. S. & Cole, R. S. (1965). J. Am. Chem. Soc., 87, 3256-3257;
4. c) Grosch, B. & Bach, T. (2004). In: Chiral Photochemistry, Inoue, Y. & Ramamurthy, V. (Eds.), Marcel Dekker: New York, Vol. 11, 315;
5. d) Elgavi, A., Green, S. B., & Schmidt, G. M. J. (1973). J. Am. Chem. Soc., 95, 2058-2059;
6. e) Scheffer, J. R. (2001). Can. J. Chem., 79, 349-357;
7. f) Toda, F. (1995). Acc. Chem. Res., 28, 480-486.
8. a) Garcia-Garibay, M., Scheffer, J. R., Trotter, J., & Wireko, F. (1989). J. Am. Chem. Soc., 111, 4985-4986;
9. b) Ohasi, Y., Sakai, Y., Sekine, A., Arai, Y., Ohgo, Y., Kamiya, N., & Iwasaki, H. (1995). Bull. Chem. Soc. Jpn., 68, 2517;
10. Leibovitch, M., Olovsson, G., Scheffer, J. R., & Trotter, J. (1997). Pure & Appl. Chem., 69, 815-823;
11. Toda, F. (1995). Acc. Chem. Res., 28, 480-486.
12. Natarajan, A., Mague, J. T., & Ramamurthy, V. (2005). J. Am. Chem. Soc., 127, 3568;
13. Natarajan, A., Mague, J. T., & Ramamurthy, V., (2005). Crystal Growth and Design, 5, 2348.
14. Ramamurthy, V., Natarajan, A., Kaanumalle, L. S., Karthikeyan, S., Sivaguru, J., Shailaja, J., & Joy, A (2004). Chiral photochemistry within zeolites. In: Chiral Photochemistry, Inoue, Y. & Ramamurthy, V., (Eds.), Marcell Dekker: New York, 563-633.
15. Sivaguru, J., Natarajan, A., Kaanumalle, L. S., Shailaja, J., Uppili, S., Joy, A., & Ramamurthy, V. (2003). Acc. Chem. Res., 36, 509-521.
16. a) Wagner, P. J., Meador, M. A., Zhou, B., & Park, B.-S. (1991). J. Am. Chem. Soc., 113, 9630;
17. b) Cheung, E., Rademacher, K., Scheffer, J. R., & Trotter, J. (2000), Tetrahedron, 56, 6739-6751.
18. Procedure for loading, photoreaction, extraction are presented in the supplementary material.
19. Kaanumalle, L. S., Sivaguru, J., Arunkumar, N., Karthikeyan, S., & Ramamurthy, V. (2003), Chem. Commun., 1, 116-117.
20. Jockusch, R. A., Lemoff, A. S., & Williams, E. R. (2001). J. Am. Chem. Soc., 123, 12255.
21. 16 was used; Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M. K., Macrae, C. P., McCabe, P., Pearson, J., & Taylor, R. (2001). Acta Crystallogr., B58, 815.
22. 1, a=9.602(6), b= 18.051(3), c=26.304(6), β=93.568(6), V=4550.3(13), Z = 8, 25334 reflections collected, R=11.0%. The crystal If was twinned and therefore averaging Friedel opposites can't be done reliably because not all symmetry equivalent reflections have the same amount of overlap (or its absence) between the twin components. Also the quality of the data set was poor due to very small crystal size.
23. Keating, A. E. & Garcia-Garibay, M. A. (1998). Photochemical solid-to-solid reactions. In: Molecular and Supramolecular Photochemistry, Ramamurthy, V. & Schanze, K. S. (Eds.), Marcel Dekker, Inc.: New York, 195-248.
24. a) Scheffer, J. R. (2004). The Solid-state ionic chiral auxiliary approach to asymmetric induction in photochemical reactions. In: Chiral Photochemistry, Ramamurthy, V. (Ed.), Marcell Dekker: New York, 463-483;
25. b) Natarajan, A., Wang, K., Ramamurthy, V., Scheffer, J. R., & Patrick, B. (2002). Org. Lett., 4, 1443-1446.