Hydroxy-directed regio- and diastereoselective [2+2] photocycloaddition (Paterno-Buchi reaction) of benzophenone to chiral allylic alcohols [8]

Journal of the American Chemical Society

Volumn 122, Issue 12, 2000, Pages 2958-2959

  Adam, Waldemar ^a   Peters, Karl ^b   Peters, Eva Maria ^b   Stegmann, Veit R ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; BENZOPHENONE;

CHIRALITY; DIASTEREOISOMER; LETTER; PHOTOOXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034728633     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994279z     Document Type: Letter

References (34)

1. Adam, W.; Wirth, T. Acc. Chem. Res. 1999, 32, 703-710.
2. (a) Adam, W.; Nestler, B. J. Am. Chem. Soc. 1992, 114, 6549-6550.
3. (b) Adam, W.; Nestler, B. J. Am. Chem. Soc. 1993, 115, 5041-5049.
4. (c) Adam, W.; Prein, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 477-494.
5. (a) Adam, W.; Prein, M. J. Am. Chem. Soc. 1993, 115, 3766-3767.
6. (b) Adam, W.; Peters, E. M.; Peters, K.; Prein, M.; von Schnering, H. G. J. Am. Chem. Soc. 1995, 117, 6686-6690.
7. (c) Adam, W.; Prein, M. Acc. Chem. Res. 1996, 29, 275-283.
8. Adam, W.; Saha-Möller, C. R.; Schambony, S. B. J. Am. Chem. Soc. 1999, 121, 1834-1838.
9. (a) Rossiter, B. E.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett. 1979, 19, 4733-4736.
10. (b) Adam, W.; Kumar, R.; Reddy, T. I.; Renz, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 880-882.
11. (c) Adam, W.; Mitchell, C. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 533-535.
12. (d) Adam, W.; Corma, A.; Reddy, T. I.; Renz, M. J. Org. Chem. 1997, 62, 3631-3637.
13. (e) Adam, W.; Degen, H.-G.; Saha-Möller, C. R. J. Org. Chem. 1999, 64, 1274-1277.
14. (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. J. Org. Chem. 1999, 64, 3699-3707.
15. (g) Adam, W.; Stegmann, V. R.; Saha-Möller, C. R. J. Am. Chem. Soc. 1999, 121, 1879-1882.
16. (a) Adam, W.; Smerz, A. K. Tetrahedron 1995, 51, 13039-13044.
17. (b) Adam, W.; Smerz, A. K. J. Org. Chem. 1996, 61, 3506-3510.
18. (a) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry: Blackwell: Oxford, 1991; Chapter 7.2.
19. (b) Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, 1991; Chapter 11.3.
20. (c) Griesbeck, A. G. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P., Eds.; CRC Press: New York, 1995; pp 550-559.
21. For a recent review see: Bach, T. Synthesis 1998, 683-703.
22. Fleming, S. A.; Gao, J. J. Tetrahedron Lett. 1997, 38, 5407-5410.
23. (a) Bach, T.; Jödicke, K.; Wibbeling, B. Tetrahedron 1996, 52, 10861-10878.
24. (b) Bach, T.; Jödicke, K.; Kather, K.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 2437-2445.
25. (c) Bach, T.; Jödicke, K.; Kather, K.; Hecht, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2271-2273.
26. Sydnes, L. K.; Hansen, K. I.; Oldroyd, D. L.; Weedon, A. C.; Jørgensen, E. Acta Chem. Scand. 1993, 47, 916-924.
27. de Mayo, P. Acc. Chem. Res. 1971, 4, 41-47.
28. Peters, K.; Peters, E. M.; Stegmann, V. R.; Adam, W. Z. Kristallograph. NCS. In press.
29. Griesbeck, A. G.; Mauder, H.; Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70-75.
30. (a) Sun, D.; Hubig, S. M.; Kochi, J. K. J. Org. Chem. 1999, 64, 4, 2250-2258.
31. (b) Hubig, S. M.; Sun, D.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1999, 781-788.
32. (c) Abe, M.; Shirodai, Y.; Nojima, M. J. Chem. Soc., Perkin Trans. 1 1998, 3253-3260.
33. (d) Hu, S.; Neckers, D. C. J. Org. Chem. 1997, 62, 6820-6826.
34. (e) Eckert, G.; Goez, M. J. Am. Chem. Soc. 1994, 116, 11999-12009.