Radical alkenylation of α-halo carbonyl compounds with alkenylindiums

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4555-4558

  Takami, Kazuaki ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENE DERIVATIVE; ALKYNE; ALKYNE DERIVATIVE; ALKYNYL GROUP; BORANE DERIVATIVE; CARBON; CARBONYL DERIVATIVE; INDIUM; STYRENE DERIVATIVE;

ALKYNYLATION; ARTICLE; CARBONYLATION; CHEMICAL BOND; QUANTUM YIELD; RADICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 10044224652     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048070o     Document Type: Article

References (29)

1. (a) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 715-831.
2. (b) Baldwin, J. E.; Kelly, D. R. Ziegler, C. B. J. Chem. Soc., Chem. Commun. 1984, 133-134.
3. (c) Baldwin, J. E.; Kelly, D. R. J. Chem. Soc., Chem. Commun. 1985, 682-684.
4. (d) Harris, F. L.; Weiler, L. Tetrahedron Lett. 1987, 28, 2941-2944.
5. (e) Curran, D. P. Synthesis 1988, 417-439.
6. (f) Curran, D. P. Synthesis 1988, 489-513.
7. (g) Keck, G. E.; Burnett, D. A. J. Org. Chem. 1987, 52, 2958-2960.
8. (h) Keck, G. E.; Byers, J. H.; Tafesh, A. M. J. Org. Chem. 1988, 53, 1127-1128.
9. (i) Kraus, G.; Andersh, B.; Su, Q.; Shi, J. Tetrahedron Lett. 1993, 34, 1741-1744.
10. (j) Gómez. A. M.; López, J. C.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1994, 1689-1695.
11. (k) Delouvrié, B.; Fensterbank. L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 121, 11395-11401.
12. (a) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986-11987.
13. (b) Clark, A. J.; Rooke, S. Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909-912.
14. (c) Bertrand, F.; Quiclet-Sire, B.; Zard, S. Z. Angew. Chem., Int. Ed. 1999, 38, 1943-1946.
15. (d)Kalaï, C.; Tate, E.; Zard, S. Z. Chem. Commun. 2002, 1430-1431.
16. Rosenstein, I. J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: New York, 2001; Vol. 1, pp 50-71.
17. (a) Takami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2002, 4, 2993-2995.
18. (b) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627-6635.
19. (c) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2003, 68, 6627-6631.
20. Baba also reported radical reactions mediated by dichloroindium radical. (a) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 2002, 124, 906-907. (b) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. Tetrahedron Lett. 2001, 42, 4461-4463. (c) Miyai, T.; Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 1998, 39, 1929-1932.
21. Baba also reported radical reactions mediated by dichloroindium radical. (a) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 2002, 124, 906-907. (b) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. Tetrahedron Lett. 2001, 42, 4461-4463. (c) Miyai, T.; Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 1998, 39, 1929-1932.
22. Baba also reported radical reactions mediated by dichloroindium radical. (a) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 2002, 124, 906-907. (b) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. Tetrahedron Lett. 2001, 42, 4461-4463. (c) Miyai, T.; Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 1998, 39, 1929-1932.
23. β-Styryllithium was prepared from β-bromostyrylene (1, E/Z = 82/ 18) and 2 equiv of tert-butyllithium. The stereochemistry of alkenylindium 2 was determined by iodolysis.
24. When a higher yield was requested, an increasing amount of 2 and injection of air into the reaction flask were particularly effective. All particulars of the reaction are shown in the Supporting Information.
25. 2 in the reaction of Scheme 2 did not show a significant effect.
26. In this case, the reaction was performed in THF with β-styryl Grignard reagent in place of β-styryllithium.
27. The same least motion mechanism has been proposed for the styryl sulfone-mediated reaction. See ref 2a.
28. The stereochemistry of alkenylindiums 14 and 17 was determined by iodolysis and deuteriolysis.
29. The stereochemistry of alkenylindium 25 was determined by iodolysis.