Carbonyl olefination utilizing an alkyl halide-titanocene(II) system

Chemical Communications

Volumn , Issue 17, 2002, Pages 1974-1975

  Takeda, Takeshi ^a   Shimane, Keiko ^a   Ito, Kenji ^a   Saeki, Naoko ^a   Tsubouchi, Akira ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; ALKYL GROUP; CARBONYL DERIVATIVE; ESTER; HALIDE; KETONE; LACTONE; ORGANOMETALLIC COMPOUND; TITANIUM DERIVATIVE; TITANOCENE;

ARTICLE; CHEMICAL MODIFICATION; REACTION ANALYSIS; SPECIES;

EID: 0036970697     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b205983e     Document Type: Article

References (25)

1. A. Maercker, Org. React., 1965, 14, 270.
2. W. S. Wadsworth Jr., Org. React., 1977, 25, 73.
3. D. J. Ager, Org. React., 1990, 38, 1.
4. P. R. Blakemore, W. J. Cole, P. J. Kocienski and A. Morley, Synlett, 1998, 26 and references therein.
5. S. H. Pine, Org. React., 1993, 43, 1.
6. S. Matsubara, K. Ukai, T. Mizuno and K. Utimoto, Chem. Lett., 1999, 825; S. Matsubara, Y. Otake, Y. Hashimoto and K. Utimoto, Chem. Lett., 1999, 747 and references therein.
7. S. Matsubara, K. Ukai, T. Mizuno and K. Utimoto, Chem. Lett., 1999, 825; S. Matsubara, Y. Otake, Y. Hashimoto and K. Utimoto, Chem. Lett., 1999, 747 and references therein.
8. M. A. Rahim, H. Sasaki, J. Saito, T. Fujiwara and T. Takeda, Chem. Commun., 2001, 625 and references therein.
9. T. Takeda, R. Sasaki and T. Fujiwara, J. Org. Chem., 1998, 63, 7286; T. Takeda, Y. Endo, A. C. S. Reddy, R. Sasaki and T. Fujiwara, Tetrahedron, 1999, 55, 2475; T. Fujiwara, M. Odaira and T. Takeda, Tetrahedron Lett., 2001, 42, 3369.
10. T. Takeda, R. Sasaki and T. Fujiwara, J. Org. Chem., 1998, 63, 7286; T. Takeda, Y. Endo, A. C. S. Reddy, R. Sasaki and T. Fujiwara, Tetrahedron, 1999, 55, 2475; T. Fujiwara, M. Odaira and T. Takeda, Tetrahedron Lett., 2001, 42, 3369.
11. T. Takeda, R. Sasaki and T. Fujiwara, J. Org. Chem., 1998, 63, 7286; T. Takeda, Y. Endo, A. C. S. Reddy, R. Sasaki and T. Fujiwara, Tetrahedron, 1999, 55, 2475; T. Fujiwara, M. Odaira and T. Takeda, Tetrahedron Lett., 2001, 42, 3369.
12. T. Takeda, K. Shimane, T. Fujiwara and A. Tsubouchi, Chem. Lett., 2002, 290.
13. The reactions of 2a with methyl iodide and benzyl bromide gave no olefination product under similar conditions. A considerable amount of diphenylethane (31%) was produced by the latter reaction suggesting that there is an alternative mode of degradation for the alkyltitanocenes 5 or6 in this system.
14. F. Z. Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999, p. 78.
15. N. A. Petasis, S.-P. Lu, E. I. Bzowej, D.-K. Fu, J. P. Staszewski, I. Akritopoulou-Zanze, M. A. Patane and Y. H. Hu, Pure Appl. Chem., 1996, 67, 667.
16. N. A. Petasis, in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim, 1998, p. 361.
17. N. A. Petasis and E. I. Bzowej, J. Am. Chem. Soc., 1990, 112, 6392; N. A. Petasis and S.-P. Lu, Tetrahedron Lett., 1995, 36, 2393; N. A. Petasis, Y.-H. Hu and D.-K. Fu, Tetrahedron Lett., 1995, 36, 6001.
18. N. A. Petasis and E. I. Bzowej, J. Am. Chem. Soc., 1990, 112, 6392; N. A. Petasis and S.-P. Lu, Tetrahedron Lett., 1995, 36, 2393; N. A. Petasis, Y.-H. Hu and D.-K. Fu, Tetrahedron Lett., 1995, 36, 6001.
19. N. A. Petasis and E. I. Bzowej, J. Am. Chem. Soc., 1990, 112, 6392; N. A. Petasis and S.-P. Lu, Tetrahedron Lett., 1995, 36, 2393; N. A. Petasis, Y.-H. Hu and D.-K. Fu, Tetrahedron Lett., 1995, 36, 6001.
20. N. A. Petasis and E. I. Bzowej, J. Org. Chem., 1992, 57, 1327.
21. N. A. Petasis and D.-K. Fu, J. Am. Chem. Soc., 1993, 115, 7208; N. A. Petasis and I. Akritopoulou, Synlett, 1992, 665; N. A. Petasis, J. P. Staszewski and D.-K. Fu, Tetrahedron Lett., 1995, 36, 3619.
22. N. A. Petasis and D.-K. Fu, J. Am. Chem. Soc., 1993, 115, 7208; N. A. Petasis and I. Akritopoulou, Synlett, 1992, 665; N. A. Petasis, J. P. Staszewski and D.-K. Fu, Tetrahedron Lett., 1995, 36, 3619.
23. N. A. Petasis and D.-K. Fu, J. Am. Chem. Soc., 1993, 115, 7208; N. A. Petasis and I. Akritopoulou, Synlett, 1992, 665; N. A. Petasis, J. P. Staszewski and D.-K. Fu, Tetrahedron Lett., 1995, 36, 3619.
24. N. A. Petasis and E. I. Bzowej, Tetrahedron Lett., 1993, 34, 943.
25. N. A. Petasis and Y.-H. Hu, J. Org. Chem., 1997, 62, 782.