High facial diastereoselectivity in the photocycloaddition of a chiral aromatic aldehyde and an enamide induced by intermolecular hydrogen bonding [13]

Journal of the American Chemical Society

Volumn 121, Issue 45, 1999, Pages 10650-10651

  Bach, Thorsten ^a   Bergmann, Hermann ^a   Harms, Klaus ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGEN BOND; LETTER; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0033579179     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992209m     Document Type: Letter

References (27)

1. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer: New York, 1991.
2. For some selected examples, see: (a) Famulok, M.; Jeong, K.-S.; Deslongchamps, G.; Rebek, J., Jr. Angew. Chem. 1991, 103, 880; Angew. Chem., Int. Ed. Engl. 1991, 30, 858. (b) Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554. (c) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823. (d) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (e) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.-y.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (f) Schrader, T. J. Am. Chem. Soc. 1998, 120, 11816.
3. For some selected examples, see: (a) Famulok, M.; Jeong, K.-S.; Deslongchamps, G.; Rebek, J., Jr. Angew. Chem. 1991, 103, 880; Angew. Chem., Int. Ed. Engl. 1991, 30, 858. (b) Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554. (c) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823. (d) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (e) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.-y.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (f) Schrader, T. J. Am. Chem. Soc. 1998, 120, 11816.
4. For some selected examples, see: (a) Famulok, M.; Jeong, K.-S.; Deslongchamps, G.; Rebek, J., Jr. Angew. Chem. 1991, 103, 880; Angew. Chem., Int. Ed. Engl. 1991, 30, 858. (b) Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554. (c) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823. (d) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (e) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.-y.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (f) Schrader, T. J. Am. Chem. Soc. 1998, 120, 11816.
5. For some selected examples, see: (a) Famulok, M.; Jeong, K.-S.; Deslongchamps, G.; Rebek, J., Jr. Angew. Chem. 1991, 103, 880; Angew. Chem., Int. Ed. Engl. 1991, 30, 858. (b) Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554. (c) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823. (d) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (e) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.-y.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (f) Schrader, T. J. Am. Chem. Soc. 1998, 120, 11816.
6. For some selected examples, see: (a) Famulok, M.; Jeong, K.-S.; Deslongchamps, G.; Rebek, J., Jr. Angew. Chem. 1991, 103, 880; Angew. Chem., Int. Ed. Engl. 1991, 30, 858. (b) Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554. (c) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823. (d) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (e) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.-y.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (f) Schrader, T. J. Am. Chem. Soc. 1998, 120, 11816.
7. For some selected examples, see: (a) Famulok, M.; Jeong, K.-S.; Deslongchamps, G.; Rebek, J., Jr. Angew. Chem. 1991, 103, 880; Angew. Chem., Int. Ed. Engl. 1991, 30, 858. (b) Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554. (c) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823. (d) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (e) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.-y.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (f) Schrader, T. J. Am. Chem. Soc. 1998, 120, 11816.
8. For some selected examples, see: (a) Famulok, M.; Jeong, K.-S.; Deslongchamps, G.; Rebek, J., Jr. Angew. Chem. 1991, 103, 880; Angew. Chem., Int. Ed. Engl. 1991, 30, 858. (b) Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554. (c) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823. (d) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (e) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.-y.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (f) Schrader, T. J. Am. Chem. Soc. 1998, 120, 11816.
9. (a) For studies in which hydrogen bonding was used for selectivity control in thermal reactions, see: Booth, C. A.; Philp, D. Tetrahedron Lett. 1998, 39, 6987 and references therein.
10. (b) For supramolecular catalysis, see: Saunders: J. K. M. Chem. Eur. J. 1998, 4, 1378 and references therein.
11. For a recent review, see: Fleming, S. A.; Bradford, C. L.; Gao, J. J. Molecular and Supramolecular Photochemistry: Organic Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Dekker: New York, 1997; Vol. 1, p 187.
12. Reviews on stereoselective photochemical reactions in the solid state: (a) Ito, Y. Synthesis 1998, 1. (b) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203. (c) Toda, F. Acc. Chem. Res. 1995, 28, 480.
13. Reviews on stereoselective photochemical reactions in the solid state: (a) Ito, Y. Synthesis 1998, 1. (b) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203. (c) Toda, F. Acc. Chem. Res. 1995, 28, 480.
14. Reviews on stereoselective photochemical reactions in the solid state: (a) Ito, Y. Synthesis 1998, 1. (b) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203. (c) Toda, F. Acc. Chem. Res. 1995, 28, 480.
15. Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1997, 119, 10237.
16. Sieburth, S. McN.; McGee, K. F., Jr.; Al-Tel, T. H. J. Am. Chem. Soc. 1998, 120, 587.
17. (b) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661.
18. Jeong, K.-S.; Parris, K.; Ballester, P.; Rebek, J., Jr. Angew. Chem. 1990, 102, 550; Angew. Chem., Int. Ed. Engl. 1990, 29, 555.
19. Jeong, K.-S.; Parris, K.; Ballester, P.; Rebek, J., Jr. Angew. Chem. 1990, 102, 550; Angew. Chem., Int. Ed. Engl. 1990, 29, 555.
20. Hubert, J. C.; Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1975, 31, 1437.
21. Bach, T. Angew. Chem. 1996, 108, 976. Angew. Chem., Int. Ed. Engl. 1996, 35, 884.
22. Bach, T. Angew. Chem. 1996, 108, 976. Angew. Chem., Int. Ed. Engl. 1996, 35, 884.
23. (b) Bach, T.; Schröder, J. J. Org. Chem. 1999, 64, 1265.
24. It was shown by NOE experiments that 4a and 5a do indeed have the same relative configuration within the oxetane ring, i.e., that the simple diastereoselectivity of the reaction is high.
25. 4a: colorless crystals; triclinic, P1, a = 814.5(1) pm, b= 1117.0(1) pm, c = 1324.1(1) pm; α = 105.191(1)°, β = 106.46°, γ = 101.38°; Z = 2; R = 4.9%; GOF = 1.046.
26. The HOSTEST program was used for determining the association constants: Wilcox, C. S. In Frontiers in Supramolecular Chemistry and Photochemistry; Schneider, H.-J., Dürr, H., Eds.; VCH: Weinheim, 1991; pp 123.
27. The given error limits represent the standard deviation obtained from applying a curve fit program (HOSTEST) to the measured data points.