Intermolecular free radical reactions on solid support. Allylation of esters

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 8929-8932

  Sibi, Mukund P ^a   Chandramouli, Sithamalli V ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; FREE RADICAL; POLYMER;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS;

EID: 0030819770     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10445-2     Document Type: Article

References (23)

1. Terret, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
2. For leading references see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
3. (b) Fruchtel, J.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1668.
4. (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1997, 53, 5643.
5. (a) Routledge, A.; Abell, C.; Balasubramanian, S. Synlett 1997, 61.
6. (b) Du, X.; Armstrong, R. W. J. Org. Chem. 1997, 62, 5678 and references cited therein.
7. (a) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 777, 10779.
8. (b) Sibi, M. P.; Ji, J.; Wu, J. H.; Gurtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200.
9. (c) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090.
10. (d) Sibi, M. P.; Ji, J. Angew. Chem. Int. Ed. Engl. 1996, 35, 190.
11. (e) Sibi, M. P.; Ji, J. Angew. Chem. Int. Ed. Engl. 1997, 36, 247.
12. (f) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063.
13. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800.
14. For general information on free radical reactions and in particular allylations see: (a) Giese, B. Radical in Organic Synthesis. Formation of Carbon-Carbon Bond, Pergamon, Oxford, 1986.
15. (b) Curran, D. P. Synthesis 1989, Part 1, p. 417; Part 2, p. 489.
16. (b) Curran, D. P. Synthesis 1989, Part 1, p. 417; Part 2, p. 489.
17. Wang, S-S. J. Am. Chem. Soc. 1973, 95, 1328.
18. Substrate 4e was prepared by coupling Wang Resin with α-bromo phenylacetic acid using DCC/DMAP.
19. Wang resin from Advanced ChemTech, Louisville, USA, (0.8-1 mmol/g) was used in all of the scale experiments.
20. Greater than 90% of the excess allyl stannane could be recovered from the reaction.
21. The reactions have not been optimized for each substituent. The low molecular weight product acids are very volatile and may account for their moderate yields.
22. 13C NMR. The analysis of the substrate on the resin was carried out by IR.
23. 1H NMR integration of the product acid (obtained by TFA cleavage of the resin) and by mass spectral analysis. A comparison of reduction data (%D incorporation) for 7a and 4b also gave similar results.