Asymmetric aldol reactions on a soluble polymeric support

Organic Letters

Volumn 2, Issue 4, 2000, Pages 531-533

  Reggelin, M ^a   Brenig, V ^a   Zur, C ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001522194     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991383c     Document Type: Article

References (20)

1. Reggelin, M; Brenig, V. Tetrahedron Lett. 1996, 37, 6851.
2. Evans, D. A.; Bartroli, J. A.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
3. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
4. Reggelin, M; Brenig, V.; Welcker, R. Tetrahedron Lett. 1998, 39, 4801.
5. Reggelin, M. Nachr. Chem. Tech. Lab. 1997, 45, 1002.
6. These problems have also been observed by others. See, for example: Harris, J. M.; Liu, Y.; Chai, S.; Andrews, M. D.; Vederas, J. C. J. Org. Chem. 1998, 63, 2407.
7. For recent reviews on the use of soluble polymers in other applications of organic synthesis, see: (a) Wentworth, P., Jr.; Janda, K. D. Chem. Commun. 1999, 1917.
8. (b) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
9. (c) Geckeler, K. E. Adv. Polym. Sci. 1995, 121, 31.
10. Kinetic studies on the aminolysis of glycine p-nitrophenyl esters with polymeric or monomeric glycine esters have shown that the reaction rate is not significantly affected by the presence of the polymer. Bayer, E.; Mutter, M.; Uhmann, R.; Polster, J.; Mauser, H. J. Am. Chem. Soc. 1974, 96, 7333.
11. First application of non-cross-linked polystyrene in organic synthesis: (a) Shemyakin, M. M.; Ovchinnikov, Y. A.; Kinyushkin, A. A. Tetrahedron Lett. 1965, 6, 2323.
12. (b) Peptide synthesis: Narita, M. Bull. Chem. Soc. Jpn. 1978, 51, 1477.
13. (c) Recent application in prostanoid chemistry: Lee, K. J.; Angulo, A.; Ghazal, P.; Janda, K. D. Org. Lett. 1999, 1, 1859.
14. (a) Mutter, M.; Hagenmaier, H.; Bayer, E. Angew. Chem., Int. Ed. Engl. 1971, 10, 811.
15. (b) Bayer, E.; Mutter, M. Nature 1972, 237, 512.
16. (c) Small molecule library synthesis on MeOPEG: Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419.
17. Douglas, S. P.; Whitfield, D. M.; Krepinsky, J. J. J. Am. Chem. Soc. 1995, 117, 2116.
18. This treatment of the polymer prior to the aldol reactions proved to be an unavoidable necessity. As expected the polyether structure retains a considerable amount of water which has to be removed thoroughly.
19. 2 solution prior to hydrogenation (Schlattner, J. M.; Mazur, R. H.; Goodmonson, O. Tetrahedron Lett. 1977, 33, 2851) was not very successful. Reggelin, M.; Brenig, V., unpublished results.
20. 2 solution prior to hydrogenation (Schlattner, J. M.; Mazur, R. H.; Goodmonson, O. Tetrahedron Lett. 1977, 33, 2851) was not very successful. Reggelin, M.; Brenig, V., unpublished results.