Radical reactions of enones with electrophilic allylstannanes

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 971-974

  Enholm, Eric J ^a   Moran, Kelley M ^a   Whitley, Paul E ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; REAGENT; TIN DERIVATIVE;

ARTICLE; CONJUGATION; REACTION ANALYSIS;

EID: 0032567893     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10717-1     Document Type: Article

References (23)

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3. (b) Ramaiah, M. Tetrahedron 1987, 43, 3541;
4. (c) Curran, D. P. Synthesis 1988, 417, 489;
5. (d) Motherwell, W.B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Academic Press: New York, 1992;
6. (e) Yamamoto, Y. Accts. Chem. Res. 1987, 20, 243.
7. (3) Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079.
8. (4) For reactions of enones with tin hydride, see: (a) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784;
9. (b) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112;
10. (c) Enholm, E. J.; Whitley, P. E. Tetrahedron Lett. 1995, 9157;
11. (d) Enholm, E. J.; Whitley, P. E. Tetrahedron Lett. 1996, 559.
12. (5) (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135;
13. (b) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon Press: Oxford, U.K. 1992.
14. (6) For reviews of ketyl radical anions, see: (a)Hirota, N. in Radical Ions, Kaiser, E. T.; Kevan, L. Eds., Wiley Interscience: New York, 1968, pp. 35-85;
15. (b) Russell, G.A. in Radical Ions, Kaiser, E. T.; Kevan, L. Eds., Wiley Interscience, New York, 1968, pp. 87-150;
16. (c) Forrester, A. R.; Hay, J. M.; Thompson, R. H. Organic Chemistry of Stable Free Radicals, Academic Press: New York, 1968, pp. 82-90.
17. (7) (a) Villieras, J.; Ramband, M. Synthesis 1982, 924;
18. (b) Baldwin, J. E.; Adlington, R. M.; Lowe, C.; O'Neal, I. A.; Sanders, G. L. J. Chem. Soc. Chem. Comm. 1988, 1030.
19. (8) (a) Krishnamurthy, R.; Kuivila, H. G. J. Org. Chem. 1986, 51, 4947;
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21. (c) Bakuris, P.; Bakuzis, M. L. F. J. Org. Chem. 1981, 46, 235.
22. (9) For a review of tin(IV) enolates, see: Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 87.
23. (10) Example Procedure: An enone (1 mmol), 2-ethylcarboxytributylallylstannane (804 mg, 2 mmol), and AIBN (33 mg, 0.2 mmol) were dissolved in freshly distilled benzene (0.5 mL). The resulting solution was degassed for 20 min with a stream of Ar gas and next refluxed for 10 hours. More AIBN (33 mg, 0.2 mmol) was added after 5 h reflux. The reaction was poured into water and extracted with ether (3 × 20 mL) and concentrated under reduced pressure. The crude oil was subjected to flash column chromatography to yield the product.