Chiral-auxiliary-induced diastereoselectivity in the [4 + 2] cycloadditions of optically active 2,2-dimethyloxazolidine derivatives of sorbic acid: A model study with singlet oxygen as the smallest dienophile

Journal of the American Chemical Society

Volumn 120, Issue 17, 1998, Pages 4091-4093

  Adam, Waldemar ^a   Güthlein, Markus ^a   Peters, E M ^b   Peters, Karl ^b   Wirth, Thomas ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINE DERIVATIVE; SINGLET OXYGEN; SORBIC ACID;

ARTICLE; CHEMICAL REACTION; CHIRALITY; PHOTOOXIDATION; STEREOCHEMISTRY;

EID: 0343960573     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980059u     Document Type: Article

References (31)

1. Stereoselective Synthesis, Methods of Organic Chemistry (Houben Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; G. Thieme: Stuttgart, New York, 1995; Vol. E 21.
2. (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876.
3. (b) Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293-318.
4. (c) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497.
5. (d) Studer, A. Synthesis 1996, 793-815.
6. (e) Ager, D. J.; Prakash, L; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
7. For C=C dienophiles, see: Jurczak, J.; Bauer, T.; Chapuis, C. In Methods of Organic Chemistry (Houben Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; G. Thieme: Stuttgart, New York, 1995; Vol. E 21, pp 2779-2798, 2853-2855, 2908-2910, 2937-2942.
8. For C=O dienophiles, see: Jurczak, J.; Bauer, T.; Chapuis, C. In Methods of Organic Chemistry (Houben Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; G. Thieme: Stuttgart, New York, 1995; Vol. E 21, pp 2919-2921.
9. For N=N dienophiles, see: (a) Orena, M. In Methods of Organic Chemistry (Houben Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E. Eds.; G. Thieme: Stuttgart, New York, 1995; Vol. E 21, pp 5538-5542. (b) Thiem, R.; Rotscheidt, K. Breitmaier, E. Synthesis 1989, 836-843.
10. For N=N dienophiles, see: (a) Orena, M. In Methods of Organic Chemistry (Houben Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E. Eds.; G. Thieme: Stuttgart, New York, 1995; Vol. E 21, pp 5538-5542. (b) Thiem, R.; Rotscheidt, K. Breitmaier, E. Synthesis 1989, 836-843.
11. For N=O Dienophiles, see: Orena, M. In Methods of Organic Chemistry (Houben Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; G. Thieme: Stuttgart, New York, 1995; Vol. E 21, pp 5581-5582.
12. (a) Adam, W.; Brünker, H.-G.; Nestler, B. Tetrahedron Lett. 1991, 32, 1957-1960.
13. (b) Adam, W.; Griesbeck, A. Synthesis 1986, 1050-1052.
14. (c) Adam, W.; Prein, M. Angew. Chem. 1996, 108, 519-538.
15. (d) Dussault, P. H.; Woller, K. R.; Hillier, M. C. Tetrahedron 1994, 50, 8929-8940.
16. (a) Kanemasa, S.; Onimura, K.; Tanaka, J. Tetrahedron: Asymmetry 1991, 2, 1185-1188.
17. (b) Kanemasa, S.; Onimura, K. Tetrahedron 1992, 48, 8631-8644.
18. (c) Kanemasa, S.; Onimura, K. Tetrahedron 1992, 48, 8645-8658.
19. (d) Kanemasa, S.; Suenaga, H.; Onimura, K. J. Org. Chem. 1994,59, 6949-6954.
20. (e) Kanemasa, S.; Ueno, K.; Onimura, K.; Kikukawa, T.; Yamamoto, H. Tetrahedron 1995, 51, 10453-10462.
21. (f) Kanemasa, S.; Nomura, M.; Yoshinaga, S.; Yamamoto, H. Tetrahedron 1995, 51, 10463-10476.
22. (a) Porter, N. A.; Bruhnke, J. D.; Wu, W.-X.; Rosenstein, I. J.; Breyer, R. A. J. Am. Chem. Soc. 1991, 113, 7788-7790.
23. (b) Porter, N. A.; Rosenstein, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W.-X.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664-7676.
24. (c) Porter, N. A.; Allen, T. R.; Breyer, R. A. J. Am. Chem. Soc. 1992, 114, 7676-7683.
25. (d) Scott, D. M.; McPhail, A. T.; Porter, N. A. J. Org. Chem. 1993, 58, 1178-1186.
26. (e) Narukawa, Y.; Juneau, K. N.; Snustad, D.; Miller, D. B.; Hegedus, L. S. J. Org. Chem. 1992, 57, 5453-5462.
27. Aubry, J.-M.; Mandard-Cazin, B.; Rougee, M.; Bensasson, R. V. J. Am. Chem. Soc. 1995, 117, 9159-9164.
28. Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1982, 12, 1285-1288.
29. The formation of carbonyl compounds was observed in the photooxygenation of methyl sorbate in ethanol: Gollnick, K. Adv. Photochem. 1968, 6, 89-94.
30. Corey, E. J.; Da Silva Jardin, P.; Rohloff, J. C. J Am. Chem. Soc. 1988, 110, 3672-3673.
31. Radl, S. Adv. Heterocycl. Chem. 1997, 67, 189-190.