[2+2] Photocycloaddition of Tetronates

Angewandte Chemie - International Edition

Volumn 42, Issue 39, 2003, Pages 4824-4826

  Kemmler, Michael ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cycloaddition; Diastereoselectivity; Lactones; Oxygen heterocycles; Photochemistry

Indexed keywords

ADDITION REACTIONS; BUTANE; PHOTOCHEMICAL REACTIONS; STEREOCHEMISTRY;

DIASTEREOSELECTIVITY;

ORGANIC ACIDS;

TETRONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; MOLECULAR INTERACTION; NUCLEAR OVERHAUSER EFFECT; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0142183583     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352171     Document Type: Article

References (39)

1. Reviews: a) R. G. Salomon, Tetrahedron 1983, 39, 485-575;
2. b) J. Mattay, R. Conrads, R. Hoffmann in Methoden der Organischen Chemie (Houben-Weyl), 4th ed., 1952-, Vol. E21c 1995, pp. 3085-3132;
3. c) P. Margaretha in Methoden der Organischen Chemie (Houben-Weyl), 4th ed., 1952-, Vol. E17e, 1997, pp. 159-162.
4. a) S. R. Raychaudhuri, S. Ghosh, R. G. Salomon, J. Am. Chem. Soc. 1982, 104, 6841-6842;
5. b) S. Ghosh, S. R. Raychaudhuri, R. G. Salomon, J. Org. Chem. 1987, 52, 83-90;
6. c) D. Patra, S. Ghosh, J. Org. Chem. 1995, 60, 2526-2531;
7. d) S. Ghosh, D. Patra, S. Samajdar, Tetrahedron 1998, 54, 1789-1800.
8. T. Meul, R. Miller, L. Tenud, Chimia 1987, 41, 73-76.
9. a) P. Margaretha, Tetrahedron 1973, 29, 1317-1319;
10. b) P. Margaretha, Chimia 1975, 29, 203-209;
11. c) S. W. Baldwin, M. T. Crimmins, P. M. Gross, Tetrahedron Lett. 1978, 19, 4197-4200;
12. d) S. W. Baldwin, T. J. Mazzuchelli, Tetrahedron Lett. 1986, 27, 5975-5978;
13. e) J. Patjens, P. Margaretha, Helv. Chim. Acta 1989, 72, 1817-1824;
14. f) R.-C. Gebel, P. Margaretha, Chem. Ber. 1990, 123, 855-858;
15. g) R.-C. Gebel, P. Margaretha, Helv. Chim. Acta 1992, 75, 1633-1638;
16. h) T. Sano, N. Koseki, T. Saitoh, Y. Horiguchi, J. Toda, F. Kiuchi, Y. Tsuda, Chem. Pharm. Bull. 1997, 45, 608-612;
17. i) T. Bach, M. Kemmler, E. Herdtweck, J. Org. Chem. 2003, 68, 1994-1997, and references therein.
18. a) K. Ohga, T. Matsuo, Bull. Chem. Soc. Jpn. 1970, 43, 3505-3510;
19. b) H. Kosugi, H. Uda, Bull. Chem. Soc. Jpn. 1980, 53, 160-168;
20. c) E. Anklam, P. Margaretha, Helv. Chim. Acta 1983, 66, 1466-1474;
21. d) K. Tomioka, M. Tanaka, K. Koga, Chem. Pharm. Bull. 1989, 37, 1201-1207;
22. e) N. Hoffmann, H. Buschmann, G. Raabe, H.-D. Scharf, Tetrahedron 1994, 50, 11167-11186;
23. f) M. Tanaka, K. Tomioka, K. Koga, Tetrahedron 1994, 50, 12829-12842;
24. g) R. Alibés, J. L. Bourdelande, J. Font, A. Gregori, T. Parella, Tetrahedron 1996, 52, 1279-1292;
25. h) F. Busqué, P. de March, M. Figuerdo, J. Font, P. Margaretha, J. Raya, Synthesis 2001, 1143-1148, and references therein.
26. a) H. Zimmer, A. Amer, C. Van Pham, D. Grob-Schmitt, J. Org. Chem. 1988, 53, 3368-3370;
27. b) J. S. Bajwa, R. C. Anderson, Tetrahedron Lett. 1990, 31, 6973-6976;
28. c) T. Sato, K. Yoshimatsu, J. Otera, Synlett 1995, 843-844;
29. d) F. F. Paintner, L. Allmendinger, G. Bauschke, Synlett 2003, 83-86.
30. 2).
31. 2O, THF, or iPrOH) added to the terminal double bond.
32. For a review, see: T. V. Hansen, Y. Stenstrøm in Organic Synthesis: Theory and Applications, Vol. 5 (Ed.: T. Hudlicky), JAI, Greenwich, 2001, pp. 1-38.
33. J. R. Anderson, R. L. Edwards, J. P. Poyser, A. J. S. Whalley, J. Chem. Soc. Perkin Trans. 1 1988, 823-831.
34. R. W. Hoffmann, G. Niel, Liebigs Ann. Chem. 1991, 1195-1201.
35. T. Bach, A. Spiegel, Eur. J. Org. Chem. 2002, 645-654.
36. P. De Mayo, Acc. Chem. Res. 1970, 3, 41-47.
37. For reviews on ring-opening reactions of cyclobutanes, see: a) H. N. C. Wong, K. L. Lau, K. F. Tam, Top. Curr. Chem. 1986, 133, 83-157;
38. b) H. N. C. Wong, G. Mann, H. M. Muchall, L. Fitjer, M. Heuschmann in Methoden der Organischen Chemie (Houben-Weyl), 4th ed., 1952-, Vol. E17e, 1997, pp. 470-610;
39. J. C. Namyslo, D. E. Kaufmann, Chem. Rev. 2003, 103, 1485-1537.