Protecting/radical translocating chiral auxiliaries: A new concept in radical-mediated asymmetric synthesis

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9162-9163

  Giraud, Luc ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINO ACID; BENZALDEHYDE; LACTIC ACID; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; INFRARED RADIATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032509347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981836b     Document Type: Article

References (23)

1. Renaud, P.; Giraud, L. Synthesis 1996, 913-926.
2. Easton, C. J. Chem. Rev. 1997, 97, 53-82.
3. For a useful discussion of the preparative aspect of radical translocation reactions, see: Curran, D. P.; Shen, W. J. Am. Chem. Soc. 1993, 115, 6051-6059.
4. For the definition of the PRT-groups, see: Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900-5902.
5. Curran, D. P.; Xu, J. Y. J. Am. Chem. Soc. 1996, 118, 3142-3147.
6. Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H. T.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898.
7. Denenmark, D.; Hoffmann, P.; Winkler, T.; Waldner, A.; De Mesmaeker, A. Synlett 1991, 621-624.
8. Denenmark, D.; Winkler, T.; Waldner, A.; De Mesmeaker, A. Tetrahedron Lett. 1992, 33, 3613-3616.
9. Williams, L.; Booth, S. E.; Undheim, K. Tetrahedron 1994, 50, 13697-13708.
10. Sato, T.; Moi, T.; Sugiyama, T.; Ishibashi, H.; Ikeda, M. Heterocycles 1994, 37, 245-248.
11. Sato, T.; Kugo, Y.; Nakaumi, E.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1995, 1801-1809.
12. Murakami, M.; Hayashi, M.; Ito, Y. Appl. Organomet. Chem. 1995, 9, 385-397.
13. Booth, S. E.; Benneche, T.; Undheim, K. Tetrahedron 1995, 51, 3665-3674.
14. Weinreb, S. M. J. Heterocycl. Chem. 1996, 33, 1437.
15. Ikeda, M.; Kugo, Y.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1996, 1819-1824.
16. Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339-3344.
17. Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339-5342.
18. A related approach using a radical translocating chiral auxiliary has been reported; however, the diastereoselectivity of the reaction has not been determined: Baldwin, J. E.; Brown, D.; Scudder, P. H.; Wood, M. E. Tetrahedron Lett. 1995, 36, 2105-2108.
19. A diastereoselective process involving a 1,5-hydrogen atom translocation starting from chiral β-amino acid derivatives has been reported: Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727-8728.
20. For reactions of 1-amidoalkyl radicals controlled by a N-centered chiral auxiliary, see: Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422.
21. Pearson, W. H.; Lindbeck, A. C.; Kampf, J. W. J. Am. Chem. Soc. 1993, 115, 2622-2636.
22. This approach is related to the principle of self-generation of stereocenters developed and reviewed by Seebach: Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
23. A similar model has been proposed for a related acyliminium ion mediated reaction: Roth, E.; Altman, J.; Kapon, M.; Benishai, D. Tetrahedron 1995, 51, 801-810.