Synthesis of a Triphenylphosphine Reagent on Non-cross-linked Polystyrene Support: Application to the Staudinger/Aza-Wittig Reaction

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3777-3779

  Charette, André B ^a   Boezio, Alessandro A ^a   Janes, Marc K ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001551649     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006432w     Document Type: Article

References (17)

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4. (b) Gololobov, Y. G.; Zhmurova, I. N.; Nasukhin, L. F. Tetrahedron 1981, 37, 437-472.
5. Scriven, E. F. V.; Thurbull, K. Chem. Rev. 1988, 88, 297-368.
6. Johnson, A. W. In Ylid Chemistry; Blomquist, A. T., Ed.; Academic Press: New York and London, 1966; Vol. 7, pp 222-236.
7. Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326-332.
8. (a) Wentworth, P., Jr.; Vandersteen, A. M.; Janda, K. D. Chem. Commun. 1997, 759-760.
9. (b) Sieber, F.; Wentworth, P., Jr.; Toker, J. D.; Wentworth, A. D.; Metz, W. A.; Reed, N. N.; Janda, K. D. J. Org. Chem. 1999, 64, 5188-5192.
10. 3-bound PEG is 0.5 mmol/g.
11. For recent examples of non-cross-linked polystyrene-supported reagents see: (a) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P. Org. Lett. 1999, 1, 689-691.
12. (b) Enholm, E. J.; Schulte, J. P. Org. Lett. 1999, 1, 1275-1277.
13. Reactions involving polymer-supported reagents often require a significant excess of the reagent.
14. The polystyrene prepared by copolymerization of styrene and 4-vinylbenzyl chloride gave a lower molecular weight polymer that was not as easily manipulated: Kondo, S.; Ohtsuka, T.; Ogura, K.; Tsuda, K. J. Macromol. Sci.-Chem. 1979, A13, 767-775.
15. Green, B.; Garson, L. R. J. Chem. Soc. C 1969, 401-406.
16. Senear, A. E.; Valient, W.; Wirth, J. J. Org. Chem. 1960, 25, 2001-2006.
17. The faster reaction observed with the soluble triphenylphosphine polymer in comparison to triphenylphosphine may be a consequence of the more electron rich phosphine (p-RO substituent of the linker).