Enantioselective photochemical reactions of 2-pyridones in solution

Organic Letters

Volumn 3, Issue 4, 2001, Pages 601-603

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

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001551420     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol007004t     Document Type: Article

References (29)

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15. Hydrogen bonds as selectivity determining devices in photocycloaddition reactions: (a) Sydnes, L. K.; Hansen, K. I.; Oldroyd, D. L.; Weedon, A. C.; Jorgensen, E. Acta Chem. Scand. 1993, 47, 916-924.
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19. Control of the diastereoselectivity in [4 + 4]-photocycloaddition reactions through hydrogen binding: (a) Sieburth, S. McN.; McGee, K. F., J.; Al-Tel, T. H. J. Am. Chem. Soc. 1998, 120, 587-588.
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21. Bach, T.; Bergmann, H.; Harms, K. J. Am. Chem. Soc. 1999, 121, 10650-10651.
22. Enantioselective [4π]-cyclization of 2-pyridones in the solid state: (a) Toda, F.; Tanaka, K. Tetrahedron Lett. 1988, 29, 4299-4302.
23. (b) Wu, L.-C; Cheer, C. J.; Olovsson, G.; Scheffer, J. R.; Trotter, J.; Wang, S.-L.; Liao, F.-L. Tetrahedron Lett. 1997, 38, 3135-3138.
24. Auxiliary-induced facial diastereoselectivity in the [4π]-cyclization of 2-pyridones: Sato, M.; Katagiri, N.; Muto, M.; Haneda, T.; Kaneko, C. Tetrahedron Lett. 1986, 27, 6091-6094.
25. 1H NMR shift reagent experiments (see narrative). The [4π]-photocyclization reactions were conducted in an analogous fashion, but they were run at a lower pyridone concentration (5 mmol/L) to avoid photodimerization. The compounds 3, 4, and 6 are known, and their analytical data have been reported (3, ref 3; 4, ref 3; 6a, ref 1c,d; 6b, ref 15; 6c, ref 2b).
26. We thank Dipl.-Chem. Oliver Simic and Prof. Dr. Carsten Bolm (RWTH Aachen) for their help with the HPLC analyses.
27. 1, a = 726.2-(1) pm, b = 854.1(1) pm, c = 3046.8(1) pm; Z = 4; R = 3.4%; GOF = 1.046.
28. Sieburth, S. McN.; Lin, C.-H.; Rucando, D. J. Org. Chem. 1999, 64, 950-953.
29. Shone, R. L.; Coker, V. M.; Moormann, A. E. J. Heterocycl. Chem. 1975, 12, 389-390.