Temporary Sulfur Connection in an Intramolecular SN2 Reaction. A Stereocontrolled Synthesis of (±)-Kainic Acid

Synlett

Volumn 1996, Issue 1, 1996, Pages 60-62

  Bachi, Mario D ^a   Melman, Artem ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001876925     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5314     Document Type: Article

References (24)

1. Bachi, M. D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.
2. Bachi, M. D.; Balanov, A.; Bar-Ner, N.; Bosch, E.; Denenmark, D.; Mizhiritskii, M. Pure and Appl. Chem. 1993, 65, 595.
3. Bachi, M. D.; Balanov, A.; Bar-Ner, N. J. Org. Chem. 1994, 59, 7752.
4. Bachi, M. D.; Melman, A. J. Org. Chem. 1995, 60, 6242.
5. All chiral compounds in this work are racemic; only one enantiomer of each pair is addressed to in the text and displayed in the structural formulas.
6. For leading strategies in the total synthesis of kainic acid see: (a) Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978.
7. (b) Takano, S.; Iwabuchi, Y; Ogasawara, K. J. Chem. Soc., Chem. Comm. 1988, 1204;
8. (c) Takano, S.; Sugihara, T.; Satoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467.
9. (d) Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1990, 46, 7263.
10. (e) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Comm. 1992, 169.
11. (f) Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279.
12. (g) Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553.
13. (h) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125.
14. (i) Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773.
15. (j) Yoo, S. E.; Lee, S. H. J. Org. Chem. 1994, 59, 6968.
16. Gaonac'h, O.; Maddaluno, J.; Chauvin, J.; Duhamel, L. J. Org. Chem. 1991, 56, 4045.
17. (a) The anti isomer of 6 was obtained as minor product (31%).
18. 2O: C, 51.95; H, 7.36; N, 6.06. Found: C, 52.04; H, 7.63; N, 5.95.
19. Temporary tethered reactions employing silicon, magnesium, or aluminum as the connecting element were studied by Stork: (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054.
20. (b) Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595; references therein.
21. Masaki, Y.; Sakuma, K.; Kaji, K. Chem. Lett. 1980, 1061.
22. Kühle, E. The chemistry of sulfenic acid; p. 46; Thieme Publishers: Stuttgart, 1973.
23. 1H NMR spectrum of 9 exhibits an upfield shield for the vinylic hydrogen atoms and the allylic methyl group.
24. Crombie, L.; Rainbow, L. J. Tetrahedron Lett. 1988, 29, 6517.