One-pot β-substitution of enones with alkyl groups to β-alkyl enones

Chemical Communications

Volumn , Issue 18, 2005, Pages 2399-2401

  Matsuo, Jun Ichi ^a   Aizawa, Yayoi ^a  

^a KITASATO INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYL GROUP; BENZENE DERIVATIVE; COPPER DERIVATIVE; ENONE DERIVATIVE; HYDROGEN; N TERT BUTYLBENZENESULFINIMIDOYL CHLORIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; HECK REACTION; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 19944414969     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b502134k     Document Type: Article

References (33)

1. T. Mizoroki, K. Mori and A. Ozaki, Bull. Chem. Soc Jpn., 1971, 44, 581;
2. R. F. Heck, Org. React., 1982, 27, 345-390;
3. R. F. Heck, Acc. Chem. Res., 1979, 12, 146-151;
4. R. F. Heck, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 4, pp. 833-863.
5. A. B. Dounay and L. E. Overman, Chem. Rev., 2003, 103, 2945-2963;
6. M. Shibasaki and E. M. Vogl, in Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, 1999, vol. 1, ch. 14, pp. 457-487;
7. M. Shibasaki, E. M. Vogl and T. Ohshima, in Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, 2004, Supplement 1, pp. 73-81.
8. Only those alkyl halides with a halide atom at a bridgehead position, such as 1-bromoadamantane, have been successfully employed in Heck reactions, see: S. Bräse. B. Waegell and A. de Meijere, Synthesis, 1998. 148-152.
9. S. A. Lebedev, V. S. Lopatina, E. S. Petrov and I. P. Beletskaya, J. Organomet. Chem., 1988, 344, 253-259.
10. B. P. Branchaud, M. S. Meier and Y. Choi, Tetrahedron Lett., 1988, 29, 167-170;
11. B. P. Branchaud and W. D. Detlefsen, Tetrahedron Lett., 1991, 32, 6273-6276;
12. Y. Ikeda, T. Nakamura, H. Yorimitsu and K. Oshima, J. Am. Chem. Soc., 2002, 124, 6514-6515.
13. E. Piers and I. Nagakura, J. Org. Chem., 1975, 40, 2694-2696;
14. E. Piers, K. F. Chens and I. Nagakura, Can. J. Chem., 1982, 60, 1256-1263.
15. G. Stork and R. L. Danheiser, J. Org. Chem., 1973, 38, 1775-1776.
16. As an another example: A. P. Kozikowski and S. H. Jung, J. Org. Chem., 1986, 51, 3400-3402.
17. H. J. Reich, J. M. Renga and I. L. Reich, J. Am. Chem. Soc., 1975, 97, 5434-5447.
18. K. C. Nicolaou, D. L. F. Gray, T. Montagnon and S. T. Harrison. Angew. Chem. Int. Ed., 2002, 41, 996-1000.
19. B. B. Snider, D. J. Rodini and J. van Straten, J. Am. Chem. Soc., 1980, 102, 5872-5880.
20. Review: J. Matsuo, J. Synth. Org. Chem. Jpn., 2004, 62, 574-583.
21. J. Matsuo, D. Iida, K. Tatani and T. Mukaiyama, Bull. Chem. Soc. Jpn., 2002, 75, 223-234;
22. J. Matsuo, H. Kitagawa, D. Iida and T. Mukaiyama, Chem. Lett., 2001, 150-151;
23. T. Mukaiyama, J. Matsuo and M. Yanagisawa, Chem. Lett., 2000, 1072-1073.
24. J. Matsuo, A. Kawana, Y. Fukuda and T. Mukaiyama, Chem. Lett., 2001, 712-713;
25. T. Mukaiyama, A. Kawana, Y. Fukuda and J. Matsuo, Chem. Lett., 2001, 390-391.
26. J. Matsuo, T. Shibata, H. Kitagawa and T. Mukaiyama, ARKIVOC, 2001, 58-65.
27. J. Matsuo and Y. Aizawa, Tetrahedron Lett., 2005, 46, 407-410;
28. T. Mukaiyama, J. Matsuo and H. Kitagawa, Chem. Lett., 2000, 1250-1251.
29. K. C. Nicolaou, T. V. Koftis, S. Vyskocil, G. Petrovic, T. Ling, Y. M. A. Yamada, W. Tang and M. O. Frederick. Angew. Chem Int. Ed., 2004, 43, 4318-4324;
30. M. Ishizaki, Y. Niimi and O. Hoshino. Tetrahedron Lett., 2003, 44, 6029-6031.
31. B. H. Lipshutz, M. Koerner and D. A. Parker, Tetrahedron Lett., 1987, 28, 945-948.
32. B. H. Lipshutz, P. Fatheree, W. Hagen and K. L. Stevens, Tetrahedron Lett., 1992, 33, 1041-1044.
33. D. Seyferth and H. M. Cohen, J. Organomet. Chem., 1963, 1, 15-21.