Diastereo- and enantioselective δ-H abstraction in the solid state of 1-benzoyl-8-benzylnaphthalene - Absolute asymmetric synthesis due to a chiral crystal environment

European Journal of Organic Chemistry

Volumn , Issue 10, 1998, Pages 2079-2082

  Irngartinger, Hermann ^a   Fettel, Peter Walter ^a   Siemund, Volker ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Asymmetric synthesis; Hydrogen transfer; Photochemistry; Solid state chemistry; Topochemistry

Indexed keywords

EID: 0001824899     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199810)1998:10<2079::aid-ejoc2079>3.0.co;2-e     Document Type: Article

References (19)

1. For reviews on AAS see: [1a] G. Kaupp, M. Haak, Angew. Chem. 1993, 105, 727-728; Angew. Chem. Int. Ed. Engl. 1993, 32, 694-695. [1b] M. Sakamoto, Chem. Eur. J. 1997, 3, 684-689. - For a new example, see: [1c] L.-C. Wu, C. J. Cheer, G. Olovsson, J. R. Scheffer, J. Trotter, S.-L. Wang, F.-L. Liao, Tetrahedron Lett. 1997, 38, 3135-3138.
2. For reviews on AAS see: [1a] G. Kaupp, M. Haak, Angew. Chem. 1993, 105, 727-728; Angew. Chem. Int. Ed. Engl. 1993, 32, 694-695. [1b] M. Sakamoto, Chem. Eur. J. 1997, 3, 684-689. - For a new example, see: [1c] L.-C. Wu, C. J. Cheer, G. Olovsson, J. R. Scheffer, J. Trotter, S.-L. Wang, F.-L. Liao, Tetrahedron Lett. 1997, 38, 3135-3138.
3. For reviews on AAS see: [1a] G. Kaupp, M. Haak, Angew. Chem. 1993, 105, 727-728; Angew. Chem. Int. Ed. Engl. 1993, 32, 694-695. [1b] M. Sakamoto, Chem. Eur. J. 1997, 3, 684-689. - For a new example, see: [1c] L.-C. Wu, C. J. Cheer, G. Olovsson, J. R. Scheffer, J. Trotter, S.-L. Wang, F.-L. Liao, Tetrahedron Lett. 1997, 38, 3135-3138.
4. For reviews on AAS see: [1a] G. Kaupp, M. Haak, Angew. Chem. 1993, 105, 727-728; Angew. Chem. Int. Ed. Engl. 1993, 32, 694-695. [1b] M. Sakamoto, Chem. Eur. J. 1997, 3, 684-689. - For a new example, see: [1c] L.-C. Wu, C. J. Cheer, G. Olovsson, J. R. Scheffer, J. Trotter, S.-L. Wang, F.-L. Liao, Tetrahedron Lett. 1997, 38, 3135-3138.
5. [2a] S. V. Evans, M. Garcia-Garibay, N. Omkaram, J. R. Scheffer, J. Trotter, F. Wireko, J. Am. Chem. Soc. 1986, 108, 5648-5650.
6. [2b] F. Toda, M. Yagi, S. Soda, J. Chem. Soc., Chem. Commun 1987, 1413-1414.
7. [2c] M. Sakamoto, M. Takahashi, T. Fujita, T. Nishio, I. Iida, S. Watanabe, J. Org. Chem. 1995, 60, 4682-4683.
8. [2d] M. Leibovitch, G. Olovsson, J. R. Scheffer, J. Trotter, J. Am Chem. Soc. 1997, 119, 1462-1463.
9. [2e] M. Sakamoto, M. Takahashi, M. Shimizu, T. Fujita, T. Nishio, I. Iida, K. Yamaguchi, S. Watanabe, J. Org. Chem. 1995, 60, 7088-7089.
10. [2f] M. Sakamoto, M. Takahashi, K. Kamiya, K. Yamaguchi, T. Fujita, S. Watanabe, J. Am. Chem. Soc. 1996, 118, 10664-10665.
11. C. D. DeBoer, W. G. Herkstroeter, A. P. Marchetti, A. G. Schultz, R. H. Schlessinger, J. Am. Chem. Soc. 1973, 95, 3963-3969.
12. G. Helmchen, Methoden Org. Chem. (Houben-Weyl), 4th ed., 1995, vol. E21a, pp. 53-56.
13. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100979. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [Fax: (internat.) + 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk].
14. HyperChem 4.5, Hypercube, Inc., Gainesville, Florida, USA, 1995.
15. P. Wagner, B.-S. Park, Org. Photochem. 1991, 11, 227-366.
16. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
17. N. J. Turro, Modern Molecular Photochemistry, Benjamm/Cummings, Menlo Park, CA, 1978. pp. 362-413.
18. A. E. Dorigo, K. N. Houk, J. Am. Chem. Soc. 1987, 109, 2195-2197, and references cited therein.
19. J. R. Scheffer, M. Garcia-Garibay, O. Nalamasu, Org. Photochem. 1987, 8, 249-347.