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DOI: 10.1039/A905040J (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1999, 2029-2036

Photoinduced diastereoselective pinacolisation of 4-oxo-4-phenylbutanamides to 4,5-dihydroxy-4,5-diphenyloctanediamides

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Ute Lindemann, Markus Neuburger, Margareta Neuburger-Zehnder, Dirk Wulff-Molder and Pablo Wessig

Abstract

The photoinduced pinacolisation of 4-oxo-4-phenylbutanamides 1 afforded 4,5-dihydroxy-4,5-diphenyloctanediamides 2 and 3 with unusual diastereoselectivities up to 83%, which depends on the amide substituent. In this reaction the solvent diethyl ether acts as a hydrogen donor. The structures of pinacols 2 and 3 were confirmed by X-ray analyses. Possible reasons for the diastereoselectivity and the preferred intermolecular hydrogen abstraction from the solvent are discussed. Products 5 and 6 obtained after irradiation of 4-oxo-4-phenylbutanoic acid 4 were identified by crystal structure determination as 2,2′-diphenyltetrahydro[2,2′]bifuranyl-5,5′-diones.

References

  1. G. Ciamician and P. Silber, Chem. Ber., 1900, 33, 2911 Search PubMed.
  2. M. B. Rubin, in CRC Handbook of Organic Photochemistry and Photobiology, eds. W. M. Horspool and P.-S. Song, CRC Press, Boca Raton, New York, London, Tokyo, 1995, p. 430 Search PubMed.
  3. H. J. Roth and M. H. ElRaie, Arch. Pharm., 1972, 305, 209 CAS; H. J. Roth, A. Abdul-Baki and T. Schrauth, Arch. Pharm., 1976, 309, 2 CAS.
  4. A. Padwa, E. Alexander and M. Niemcyzk, J. Am. Chem. Soc., 1969, 91, 456 CrossRef CAS.
  5. P. Wessig, P. Wettstein, B. Giese, M. Neuburger and M. Zehnder, Helv. Chim. Acta, 1994, 77, 829 CrossRef CAS; A. Steiner, P. Wessig and K. Polborn, Helv. Chim. Acta, 1996, 79, 1843 CrossRef CAS; P. Wessig and J. Schwarz, Helv. Chim. Acta, 1998, 81, 1803 CrossRef CAS; U. Lindemann, D. Wulff-Molder and P. Wessig, Tetrahedron: Asymmetry, 1998, 9, 4459 CrossRef CAS.
  6. A. Azzouzi, M. Dufour, J.-C. Gramain and R. Remuson, Heterocycles, 1988, 27, 133 CAS.
  7. U. Lindemann, G. Reck, D. Wulff-Molder and P. Wessig, Tetrahedron, 1998, 54, 2529 CrossRef CAS.
  8. H. Haber, H. Buchholz, R. Sukale and H.-G. Henning, J. Prakt. Chem., 1985, 327, 51 CrossRef CAS.
  9. H. J. Roth, M. H. ElRaie and T. Schrauth, Arch. Pharm., 1974, 307, 584 CAS.
  10. H.-G. Henning, R. Berlinghoff, A. Mahlow, H. Köppel and K.-D. Schleinitz, J. Prakt. Chem., 1981, 323, 914 CAS.
  11. F. Zymalkowski and J. Gelberg, Arch. Pharm., 1966, 299, 545 CAS.
  12. T. Hasegawa, K. Mukai, K. Mizukoshi and M. Yoshioka, Bull. Chem. Soc. Jpn., 1990, 63, 3348 CAS.
  13. C. C. Price and A. J. Tomisek, J. Am. Chem. Soc., 1942, 64, 2727 CrossRef CAS.
  14. H. G. O. Becker, H. Böttcher, F. Dietz, D. Rehorek, G. Roewer, K. Schiller and H.-J. Timpe, Einführung in die Photochemie, Deutscher Verlag der Wissenschaften, Berlin, 1991, (a)p. 457, (b)p. 370 Search PubMed.
  15. T. J. Burkey, M. Majewski and D. Griller, J. Am. Chem. Soc., 1986, 108, 2218 CrossRef CAS.
  16. P. J. Wagner, J. Am. Chem. Soc., 1967, 89, 5898 CrossRef CAS; P. J. Wagner, I. E. Kochevar and A. E. Kemppainen, J. Am. Chem. Soc., 1972, 94, 7489 CrossRef CAS.
  17. F. Kernchen, PhD Thesis, and Humboldt-Universität zu Berlin, 1986.
  18. H. Paul and H. Fischer, Helv. Chim. Acta, 1973, 56, 1575 CAS.
  19. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN98, Revision A.3, Gaussian, Inc., Pittsburgh, PA, 1998 Search PubMed.
  20. A. Peyman, H.-D. Beckhaus, D. Kramer, K. Peters, H. G. von Schnering and C. Rüchardt, Chem. Ber., 1991, 124, 1989 CAS.
  21. J. C. Woodbrey, J. Am. Chem. Soc., 1962, 84, 13 CrossRef CAS; M. Rabinowitz, J. Am. Chem. Soc., 1969, 91, 1585 CrossRef CAS.
  22. N. H. Cromwell and K. E. Cook, J. Am. Chem. Soc., 1958, 80, 4577 CrossRef.
  23. L. Andrews, J. A. Harvey, B. J. Kelsall and D. C. Duffey, J. Am. Chem. Soc., 1981, 103, 6415 CrossRef CAS.
  24. M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart and J. A. Pople, GAUSSIAN92, Revision G.2, Gaussian Inc., Pittsburgh, PA, 1992 Search PubMed.