Enantioselective Synthesis of Protected α-Hydroxy Aldehydes and Related 1,2-Amino Alcohols. Applications to the Synthesis of (-)-exo- and (-)-endo-Brevicomin

Synlett

Volumn 1996, Issue 8, 1996, Pages 731-733

  Vettel, Stephan ^a   Lutz, Christian ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001857096     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5518     Document Type: Article

References (37)

1. Hanessian, S. Total Synthesis of Natural Products: The "Chiron" Approach; Pergamon Press, Oxford, 1983.
2. Cahiez, G.; Métais, E.; Tetrahedron Lett. 1995, 36, 6449 and references cited herein.
3. (a) Rozema, M. J.; AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
4. (b) Brieden, W.; Ostwald, R.; Knochel, P. Angew. Chem 1993, 105, 629; Angew. Chem., Int. Ed. Engl. 1993, 32, 582.
5. (b) Brieden, W.; Ostwald, R.; Knochel, P. Angew. Chem 1993, 105, 629; Angew. Chem., Int. Ed. Engl. 1993, 32, 582.
6. (c) Knochel, P.; Brieden, W.; Eisenberg, C.; Rozema, M. J. Tetrahedron Lett. 1993, 34, 5881.
7. (d) Nowotny, S.; Vettel, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 4539.
8. (e) Eisenberg, C.; Knochel, P. J. Org. Chem. 1994, 59, 3760.
9. (f) Vettel, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849.
10. (g) Lütjens, H.; Knochel, P. Tetrahedron: Asymmetry 1994, 5, 1161.
11. (h) Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143.
12. (i) Schwink, L.; Knochel, P. Tetrahedron Lett. 1994, 35, 9007.
13. (j) Berninger, J.; Koert, U.; Eisenberg-Höhl, C.; Knochel, P. Chem. Ber. 1995, 128, 1021.
14. (k) Lütjens, H.; Nowotny, S.; Knochel, P. Tetrahedron: Asymmetry 1995, 6, 2675.
15. (a) Yoshioka, M.; Kawakita, T.; Ohno, M. Tetrahedron Lett. 1989, 30, 1657.
16. (b) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095.
17. (c) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691.
18. 1H-NMR analysis of the corresponding O-acetyl-mandelates using (S)-(+)-O-acetyl-mandelic acid. In each case, a calibration sample using (±)-O-acetyl-mandelic acid was prepared: Parker, D. J. Chem. Soc., Perkin Trans. 2 1983, 83.
19. 1H-NMR).
20. Abnormal ozonolysis is obtained for allylic alcohols with electron donating protecting groups like benzyl or trialkylsilyl: (a) Young, W. G; McKinnis, A. C.; Webb, I. D.; Roberts, J. D. J. Am. Chem. Soc. 1946, 68, 293. (b) Bailey, P. S. Ozonation In Organic Chemistry, Vol. I; Acadamic Press: New York, 1978.
21. Abnormal ozonolysis is obtained for allylic alcohols with electron donating protecting groups like benzyl or trialkylsilyl: (a) Young, W. G; McKinnis, A. C.; Webb, I. D.; Roberts, J. D. J. Am. Chem. Soc. 1946, 68, 293. (b) Bailey, P. S. Ozonation In Organic Chemistry, Vol. I; Acadamic Press: New York, 1978.
22. Minato, M.; Yamamoto, K.; Tsuji, J. J. Org. Chem. 1990, 55, 766.
23. 13C-NMR).
24. Mattson, R. J.; Pham, K. M.; Leuck, D. J.; Cowen, K. A. J. Org. Chem. 1990, 55, 2552.
25. 2 and following the reaction sequence described above.
26. Review: Mori, K. in The Total Synthesis of Natural Products, Vol. 4 (Syntheses up to 1979) and Vol. 9 (Syntheses from 1979-1989), Ed. ApSimon, J.; J. Wiley: New York, 1989.
27. (a) Mori, K. Tetrahedron 1974, 30, 4223.
28. (b) Mulzer, J.; Angermann, A.; Münch, W. Liebigs Ann. Chem. 1986, 825.
29. (b) Soderquist, J. A., Rane, A. M. Tetrahedron Lett. 1993, 34, 5031.
30. 13C-NMR.
31. For addition of organometallic compounds to α-hydroxy carbonyl compounds see: Devant, R. M.; Radunz, H.-E. in Houben-Weyl, Methods of Organic Chemistry , Vol. E 21b, p. 1196; Eds. Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme: Stuttgart, 1995.
32. For other asymmetric catalyzed addition of diorganozincs to α-silyloxy aldehydes see: (a) Soai, K.; Shimada, C.; Takeuchi, M.; Itabashi, M. J. Chem. Soc., Chem. Commun. 1994, 567 and ref. 3e. For other asymmetric catalyzed addition of diorganozincs to β- and γ-silyloxy aldehydes, see ref. 3c and 3f.
33. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
34. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
35. 2O, ref. 13b: -79.4).
36. (a) Stadtmüller, H.; Knochel, P. Synlett 1995, 463.
37. (b) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231.