Investigations of the asymmetric intramolecular [2 + 2] photocycloaddition and its application as a simple access to novel C2-symmetric chelating bisphosphanes bearing a cyclobutane backbone

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6127-6135

  Haag, Dieter ^a   Scharf, Hans Dieter ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029812370     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960556y     Document Type: Article

References (42)

1. (a) Ojima, I. Catalytic Asymmetric Syntheses; VCH Publishers: Weinheim, 1993.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Syntheses, J. Wiley & Sons: New York, 1994.
3. (a) Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
4. (b) Kagan, H. B. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press, Oxford, 1982; Vol. 8, p 463.
5. (a) Aviron-Violet, P.; Colleuille, Y.; Varagnat, J. J. Mol. Catal. 1979, 5, 41.
6. (b) Glaser, R.; Geresh, S.; Twaik, M. Isr. J. Chem. 1980, 20, 102.
7. (a) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1978, 100, 4321.
8. (b) Brown, J. M.; Chaloner, P. A.; Glaser, R.; Geresh, S. Tetrahedron 1980, 36, 815.
9. Morimoto, T.; Nakajima, M.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 75.
10. Ahmad, S. Tetrahedron Lett. 1991, 32, 6997.
11. Green, B. S.; Hagler, A. T.; Rabinsohn, Y.; Rejtö, M Isr. J. Chem. 1976/77, 15, 124.
12. Berens, U.; Leckel, D.; Oepen, S. C. J. Org. Chem. 1995, 60, 8204.
13. For other publications dealing with the transacetalization of vicinal diols with α-dicarbonyl compounds see: (a) Ley, S. V.; Leslie, R.; Tiffin, P. D.; Woods, M. Tetrahedron Lett. 1992, 33, 4767. (b) Ley, S. V.; Boons, G.-J.; Leslie, R.; Woods, M.; Hollinshead, D. M. Synthesis 1993, 689. (c) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. Tetrahedron: Asymmetry 1995, 6, 2113. (d) Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897.
14. For other publications dealing with the transacetalization of vicinal diols with α-dicarbonyl compounds see: (a) Ley, S. V.; Leslie, R.; Tiffin, P. D.; Woods, M. Tetrahedron Lett. 1992, 33, 4767. (b) Ley, S. V.; Boons, G.-J.; Leslie, R.; Woods, M.; Hollinshead, D. M. Synthesis 1993, 689. (c) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. Tetrahedron: Asymmetry 1995, 6, 2113. (d) Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897.
15. For other publications dealing with the transacetalization of vicinal diols with α-dicarbonyl compounds see: (a) Ley, S. V.; Leslie, R.; Tiffin, P. D.; Woods, M. Tetrahedron Lett. 1992, 33, 4767. (b) Ley, S. V.; Boons, G.-J.; Leslie, R.; Woods, M.; Hollinshead, D. M. Synthesis 1993, 689. (c) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. Tetrahedron: Asymmetry 1995, 6, 2113. (d) Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897.
16. For other publications dealing with the transacetalization of vicinal diols with α-dicarbonyl compounds see: (a) Ley, S. V.; Leslie, R.; Tiffin, P. D.; Woods, M. Tetrahedron Lett. 1992, 33, 4767. (b) Ley, S. V.; Boons, G.-J.; Leslie, R.; Woods, M.; Hollinshead, D. M. Synthesis 1993, 689. (c) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. Tetrahedron: Asymmetry 1995, 6, 2113. (d) Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897.
17. Costanzo, M. J.; Almond, H. R.; Gauthier, A. D.; Maryanoff, B. E. Tetrahedron Asymmetry 1994, 5, 2459.
18. (a) Haag, D.; Scharf, H.-D.; Raabe, G. Acta Crystallogr., Sect. C. to be submitted.
19. (b) Haag, D.; Scharf, H.-D.; Raabe, G. Acta Crytstallogr., Sect. C, to be submitted.
20. Stoermer, B.; Bacher, F. Chem. Ber. 1922, 55, 1860.
21. (a) Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Plath, M. W.; Runsink, J. J. Am. Chem. Soc. 1989, 111, 5367.
22. (b) Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem. 1991, 103, 480; Angew. Chem., Int. Ed. Engl. 1991, 30, 477.
23. (b) Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem. 1991, 103, 480; Angew. Chem., Int. Ed. Engl. 1991, 30, 477.
24. (a) Exner, O.; Giese, B. Angew. Chem. 1978, 90, 816; Angew. Chem., Int. Ed. Engl. 1978, 17, 775.
25. (a) Exner, O.; Giese, B. Angew. Chem. 1978, 90, 816; Angew. Chem., Int. Ed. Engl. 1978, 17, 775.
26. (b) Giese, B. Acc. Chem. Res. 1984, 17, 438.
27. (a) Loutfy, R. O.; De Mayo, P. J. Am. Chem. Soc. 1977, 99, 3559.
28. (b) Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1991, 113, 8525.
29. Hoffmann, N.; Buschmann, H.; Raabe, G.; Scharf, H.-D. Tetrahedron 1994, 50, 11167.
30. (a) Lewis, F. D.; Quillen, S. L.; Hale, P. D.; Oxman, J. D. J. Am. Chem. Soc. 1988, 110, 1261.
31. (b) Takagi, K.; Itoh, M.; Usami, H.; Imae, T.; Sawaki, Y. J. Chem. Soc. Perkin Trans. 2 1994, 1003.
32. Neises, B.; Steglich, W. Angew. Chem. 1978, 90, 556; Angew. Chem., Int. Ed. Engl. 1978, 17, 522.
33. Neises, B.; Steglich, W. Angew. Chem. 1978, 90, 556; Angew. Chem., Int. Ed. Engl. 1978, 17, 522.
34. The equilibrium between s-cis and s-trans conformers of α,β-enal complexes is also discussed to be a relevant factor determining the selectivity of catalytic Diels-Alder reactions: (a) Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127. (b) Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290.
35. The equilibrium between s-cis and s-trans conformers of α,β-enal complexes is also discussed to be a relevant factor determining the selectivity of catalytic Diels-Alder reactions: (a) Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127. (b) Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290.
36. Brisset, H.; Gourdel, Y.; Pellon, P.; Le Corre, M. Tetrahedron Lett. 1993, 34, 4523.
37. (21 ) McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319.
38. Rüdiger Selke, Max-Planck-Gesellschaft AG "Asymmetrische Katalyse" an der Universität Rostock, Germany.
39. (a) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171.
40. (b) Ito, Y. N.; Ariza, X.; Beck, A. K.; Bohac, A.; Ganter, C.; Gawley, R. E.; Kuhnle, F. N. M.; Tuleja, J.; Wang, Y. M.; Seebach, D. Helv. Chim. Acta 1994, 77, 2071.
41. Treibs, W.; Orttmann, H. Chem. Ber. 1960, 93, 545.
42. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.