Ytterbium mediated coupling of α-oxonitriles with allylbromides: Convenient synthesis of β,γ-unsaturated ketones

New Journal of Chemistry

Volumn 27, Issue 7, 2003, Pages 1038-1040

  Gohain, Mukut ^a   Gogoi, Baikuntha J ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^b  

^a REGIONAL RESEARCH LABORATORY   (India)

^b PUNJABI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CYANIDE; KETONE DERIVATIVE; NITRILE; TETRAHYDROFURAN; YTTERBIUM;

ANALYTIC METHOD; ARTICLE; MELTING POINT; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0043169464     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b302491c     Document Type: Article

References (26)

1. E. E. Blaise, C. R. Hebd. Séances Acad. Sci., 1901, 132, 38.
2. G. Cardillio, A. D. Simone, A. A. Mingardi and C. Tomasini, Synlett., 1995, 1131 and references cited therein; M. Demuth and G. Mikhail, Synthesis, 1989, 145.
3. G. Cardillio, A. D. Simone, A. A. Mingardi and C. Tomasini, Synlett., 1995, 1131 and references cited therein; M. Demuth and G. Mikhail, Synthesis, 1989, 145.
4. D. S. Noyce and M. Evett, J. Org. Chem., 1972, 37, 394; J. C. Aumiller and J. A. Whittle, J. Org. Chem., 1976, 41, 2959; J. K. Groves, Chem. Soc. Rev., 1972, 1, 73 . For the interconversion of α,β- and β,γ-unsaturated ketones, see: W. R. Nees, E. Loeser, R. Kirdani and J. Marsh, Tetrahedron, 1963, 19, 299; S. K. Malhotra and H. J. Ringold, J. Am. Chem. Soc., 1965, 87, 3228.
5. D. S. Noyce and M. Evett, J. Org. Chem., 1972, 37, 394; J. C. Aumiller and J. A. Whittle, J. Org. Chem., 1976, 41, 2959; J. K. Groves, Chem. Soc. Rev., 1972, 1, 73 . For the interconversion of α,β- and β,γ-unsaturated ketones, see: W. R. Nees, E. Loeser, R. Kirdani and J. Marsh, Tetrahedron, 1963, 19, 299; S. K. Malhotra and H. J. Ringold, J. Am. Chem. Soc., 1965, 87, 3228.
6. D. S. Noyce and M. Evett, J. Org. Chem., 1972, 37, 394; J. C. Aumiller and J. A. Whittle, J. Org. Chem., 1976, 41, 2959; J. K. Groves, Chem. Soc. Rev., 1972, 1, 73 . For the interconversion of α,β- and β,γ-unsaturated ketones, see: W. R. Nees, E. Loeser, R. Kirdani and J. Marsh, Tetrahedron, 1963, 19, 299; S. K. Malhotra and H. J. Ringold, J. Am. Chem. Soc., 1965, 87, 3228.
7. D. S. Noyce and M. Evett, J. Org. Chem., 1972, 37, 394; J. C. Aumiller and J. A. Whittle, J. Org. Chem., 1976, 41, 2959; J. K. Groves, Chem. Soc. Rev., 1972, 1, 73 . For the interconversion of α,β- and β,γ-unsaturated ketones, see: W. R. Nees, E. Loeser, R. Kirdani and J. Marsh, Tetrahedron, 1963, 19, 299; S. K. Malhotra and H. J. Ringold, J. Am. Chem. Soc., 1965, 87, 3228.
8. D. S. Noyce and M. Evett, J. Org. Chem., 1972, 37, 394; J. C. Aumiller and J. A. Whittle, J. Org. Chem., 1976, 41, 2959; J. K. Groves, Chem. Soc. Rev., 1972, 1, 73 . For the interconversion of α,β- and β,γ-unsaturated ketones, see: W. R. Nees, E. Loeser, R. Kirdani and J. Marsh, Tetrahedron, 1963, 19, 299; S. K. Malhotra and H. J. Ringold, J. Am. Chem. Soc., 1965, 87, 3228.
9. (a) P. Beak and K. R. Berger, J. Am. Chem. Soc., 1980, 102, 3848
10. (b) H. M. R. Hoffman and T. Tsushima, J. Am. Chem. Soc., 1877, 99, 6008.
11. M. Ouaka, T. Goto and T. Mukaiyama, Chem. Lett., 1979, 1483.
12. M. Zaidlewicz, Synthesis, 1988, 701.
13. A. Hosomi, H. Hashimoto and H. Sakurai, J. Org. Chem., 1978, 43, 2551; M. Laguerre, J. Dumogues and R. Calas, Tetrahedron Lett., 1980, 21, 831; Y. Hayashi, M. Konishi, H. Ito and M. Kamuda, J. Am. Chem. Soc., 1982, 104, 4962.
14. A. Hosomi, H. Hashimoto and H. Sakurai, J. Org. Chem., 1978, 43, 2551; M. Laguerre, J. Dumogues and R. Calas, Tetrahedron Lett., 1980, 21, 831; Y. Hayashi, M. Konishi, H. Ito and M. Kamuda, J. Am. Chem. Soc., 1982, 104, 4962.
15. A. Hosomi, H. Hashimoto and H. Sakurai, J. Org. Chem., 1978, 43, 2551; M. Laguerre, J. Dumogues and R. Calas, Tetrahedron Lett., 1980, 21, 831; Y. Hayashi, M. Konishi, H. Ito and M. Kamuda, J. Am. Chem. Soc., 1982, 104, 4962.
16. T. Sato, T. Kawara, A. Nishizawa and T. Fujisawa, Tetrahedron Lett., 1980, 21, 3377.
17. J. S. Hegedus, P. M. Kendall, S. M. La and J. R. Sheats, J. Am. Chem. Soc., 1975, 97, 5448.
18. G. Cahiez and B. Laboue, Tetrahedron Lett., 1989, 30, 7369.
19. A. N. Kasatkin, A. N. Kalak and G. A. Tolstikov, J. Organomet. Chem., 1988, 346, 23.
20. R. C. Larock and Y. La, J. Org. Chem., 1993, 58, 2846.
21. M. Shibasaki and N. Yoshikawa, Chem. Rev., 2002, 102, 2187; S. Kobayashi, M. Sugiura, H. Kitagawa and W. Lam, Chem. Rev., 2002, 102, 2227; G. A. Molander, Chem. Rev., 1992, 92, 29.
22. M. Shibasaki and N. Yoshikawa, Chem. Rev., 2002, 102, 2187; S. Kobayashi, M. Sugiura, H. Kitagawa and W. Lam, Chem. Rev., 2002, 102, 2227; G. A. Molander, Chem. Rev., 1992, 92, 29.
23. M. Shibasaki and N. Yoshikawa, Chem. Rev., 2002, 102, 2187; S. Kobayashi, M. Sugiura, H. Kitagawa and W. Lam, Chem. Rev., 2002, 102, 2227; G. A. Molander, Chem. Rev., 1992, 92, 29.
24. P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693.
25. N. Fujiwara and Y. Yamamoto, J. Org. Chem., 1999, 64, 4095.
26. H. des Abbayes and H. Alper, J. Am. Chem. Soc., 1977, 99, 98.