Diastereoselective addition of α-hydroxyalkyl and α-alkoxyalkyl radicals to chiral 4-methyleneoxazolidin-5-ones

Tetrahedron

Volumn 54, Issue 21, 1998, Pages 5709-5720

  Pyne, Stephen G ^a   Schafer, Karl ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYLENEOXAZOLIDIN 5 ONE; OXAZOLIDINE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DERIVATIZATION; DRUG SYNTHESIS; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032554849     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00259-2     Document Type: Article

References (23)

1. 1. Nair, S. A.; Lee, B.; Hangauer, Synthesis 1995, 810.
2. 2. Koch, T.; Buchardt, O. Synthesis 1993, 1065.
3. 3. Barclay, F.; Chrystal, E.; Gani, D. J. Chem. Soc., Perkin Trans 1 1996, 683.
4. 4. Garner, P. P.; Cox, P. B.; Klippenstein, S. J. J. Am. Chem. Soc. 1995, 117, 4183. Garner, P.; Leslie, R.; Anderson, J. T. J. Org. Chem. 1996, 61, 6754.
5. 4. Garner, P. P.; Cox, P. B.; Klippenstein, S. J. J. Am. Chem. Soc. 1995, 117, 4183. Garner, P.; Leslie, R.; Anderson, J. T. J. Org. Chem. 1996, 61, 6754.
6. 5. Zimmermann, J., Seebach, D., Helv. Chim. Acta. 1987 70, 1104.
7. 6. Pyne, S. G., Dikic, B., Gordon, P., Skelton, B. W., White, A. H. Aust. J. Chem. 1993, 46, 73.
8. 7. Gomez, A. M.; Mantecon, Valverde, S.; Lopez, J. C. J. Org. Chem. 1997, 62, 6612.
9. 8. Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. Clark, A. J.; Rooke, S.; Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909. Ogura, K.; Yanagisawa, A.; Fujino, T.; Takahashi, K.Tetrahedron Lett. 1988, 29, 5387.
10. 8. Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. Clark, A. J.; Rooke, S.; Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909. Ogura, K.; Yanagisawa, A.; Fujino, T.; Takahashi, K.Tetrahedron Lett. 1988, 29, 5387.
11. 8. Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. Clark, A. J.; Rooke, S.; Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909. Ogura, K.; Yanagisawa, A.; Fujino, T.; Takahashi, K.Tetrahedron Lett. 1988, 29, 5387.
12. 9. Axon, J. R.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1995, 549.
13. 10. Dofour, M.; Gramain, J.-C.; Husson, H.-P.; Sinibaldi, M.-E.; Trion, Y. Tetrahedron Lett. 1989, 30, 3429.
14. 11. Ibrahim-Ouali, M.; Sinibaldi, M.-E.; Trion, Y.; Gramain, J.-C. Tetrahedron Lett. 1996, 37, 37.
15. 12. Greenstein, J. P.; Winitz, M. Chemistry of the Amino Acids, Wiley: New York, 1961; pp 2612-2616, 2638.
16. 13. Jacob, M.; Roumestant, M. L.; Viallefont, P.; Martinez, J. Synlett 1997, 691.
17. 14. Gull, R.; Schöllkopf, U. Synthesis 1985, 1052.
18. 15. Matzinger, P.; Catalfomo, Ph.; Eugster, C. H. Helv. Chim. Acta, 1972, 55, 1478.
19. 16. Harding, K. E.; Marman, T. H.; Nam, D.-H. Tetrahedron 1988, 44, 5605.
20. 17. Ariza, J.; Font, J.; Ortuno, R. A. Tetrahedron 1990, 46, 1931.
21. 18. Schmeck, C.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 9927.
22. 19. For related studies see: Jackson, R. F. W.; Rettie, A. B.; Wood, A.; Wythes, M.J. J. Chem. Soc. Perkin Trans. 1, 1994, 1719.
23. 20. For a recent application of 2 for the synthesis of amino acids in high enantiomeric purities see: Pyne, S. G.; Schafer, K.; Skelton, B. W.; White, A. H. J. Chem. Soc., Chem. Commun. 1997, 2267.