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Volumn 7, Issue 4, 2005, Pages 649-651

Radical trifluoromethylation of titanium ate enolate

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; TITANIUM DERIVATIVE;

EID: 14844358600     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047565a     Document Type: Article
Times cited : (85)

References (48)
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    • Some reactions involving titanium ate enolates: (a) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722-5728. (b) Bernardi, A.; Cavicchioli, M.; Marchionni, C.; Potenza, D.; Scolastico, C. J. Org. Chem. 1994, 59, 3690-3694. (c) Yachi, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 1999, 121, 9465-9466. (d) Han, Z.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 2000, 41, 4415-4418.
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    • Some reactions involving titanium ate enolates: (a) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722-5728. (b) Bernardi, A.; Cavicchioli, M.; Marchionni, C.; Potenza, D.; Scolastico, C. J. Org. Chem. 1994, 59, 3690-3694. (c) Yachi, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 1999, 121, 9465-9466. (d) Han, Z.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 2000, 41, 4415-4418.
    • (1994) J. Org. Chem. , vol.59 , pp. 3690-3694
    • Bernardi, A.1    Cavicchioli, M.2    Marchionni, C.3    Potenza, D.4    Scolastico, C.5
  • 28
    • 0033552258 scopus 로고    scopus 로고
    • Some reactions involving titanium ate enolates: (a) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722-5728. (b) Bernardi, A.; Cavicchioli, M.; Marchionni, C.; Potenza, D.; Scolastico, C. J. Org. Chem. 1994, 59, 3690-3694. (c) Yachi, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 1999, 121, 9465-9466. (d) Han, Z.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 2000, 41, 4415-4418.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9465-9466
    • Yachi, K.1    Shinokubo, H.2    Oshima, K.3
  • 29
    • 0034621998 scopus 로고    scopus 로고
    • Some reactions involving titanium ate enolates: (a) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722-5728. (b) Bernardi, A.; Cavicchioli, M.; Marchionni, C.; Potenza, D.; Scolastico, C. J. Org. Chem. 1994, 59, 3690-3694. (c) Yachi, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 1999, 121, 9465-9466. (d) Han, Z.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 2000, 41, 4415-4418.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4415-4418
    • Han, Z.1    Yorimitsu, H.2    Shinokubo, H.3    Oshima, K.4
  • 30
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    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 5259-5262
    • Reetz, M.T.1    Wenderoth, B.2
  • 31
    • 0000044737 scopus 로고
    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1985) Chem. Ber. , vol.118 , pp. 1421-1440
    • Reetz, M.T.1    Westermann, J.2    Steinbach, R.3    Wenderoth, B.4    Peter, R.5    Ostarek, R.6    Maus, S.7
  • 32
    • 84984158283 scopus 로고
    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1985) Chem. Ber. , vol.118 , pp. 1441-1454
    • Reetz, M.T.1    Steinbach, R.2    Westermann, J.3    Peter, R.4    Wenderoth, B.5
  • 33
    • 0001100248 scopus 로고
    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1988) Chem. Pharm. Bull. , vol.36 , pp. 803-806
    • Takahashi, H.1    Kawabata, A.2    Niwa, H.3    Higashiyama, K.4
  • 34
    • 85082553755 scopus 로고
    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1988) Synthesis , pp. 238-240
    • Takahashi, H.1    Tsubuki, T.2    Higashiyama, K.3
  • 35
    • 0026084811 scopus 로고
    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1991) Chem. Pharm. Bull. , vol.39 , pp. 260-265
    • Takahashi, H.1    Tsubuki, T.2    Higashiyama, K.3
  • 36
    • 0027444988 scopus 로고
    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1993) Tetrahedron , vol.49 , pp. 10913-10916
    • Bernardi, A.1    Cavicchioli, M.2    Scolastico, C.3
  • 37
    • 0028133559 scopus 로고
    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 6357-6360
    • Bernardi, A.1    Marchionni, C.2    Pilati, T.3    Scolastico, C.4
  • 38
    • 0029089610 scopus 로고
    • Some reactions involving other titanium ate comlexes: (a) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262. (b) Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440. (c) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454. (d) Takahashi, H.; Kawabata, A.; Niwa, H.; Higashiyama, K. Chem. Pharm. Bull. 1988, 36, 803-806. (e) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1988, 238-240. (f) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265. (g) Bernardi, A.; Cavicchioli, M.; Scolastico, C. Tetrahedron 1993, 49, 10913-10916. (h) Bernardi, A.; Marchionni, C.; Pilati, T.; Scolastico, C. Tetrahedron Lett. 1994, 35, 6357-6360. (i) Mahrwald, R. Tetrahedron 1995, 51, 9015-9022.
    • (1995) Tetrahedron , vol.51 , pp. 9015-9022
    • Mahrwald, R.1
  • 41
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    • note
    • 9b showed that the ketone was formed in the generation of the titanium ate enolate (although this is only mentioned in the foot note of Figure 2). This fact also supports the proposed mechanism.
  • 42
    • 0000449913 scopus 로고
    • Review of the construction of quaternary carbon centers: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460. (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401. (d) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
    • (1980) Tetrahedron , vol.36 , pp. 419-460
    • Martin, S.F.1
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    • Review of the construction of quaternary carbon centers: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460. (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401. (d) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
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    • 0032473509 scopus 로고    scopus 로고
    • Review of the construction of quaternary carbon centers: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460. (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401. (d) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 388-401
    • Corey, E.J.1    Guzman-Perez, A.2
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    • 0344064789 scopus 로고    scopus 로고
    • Review of the construction of quaternary carbon centers: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460. (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401. (d) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
    • (2003) Tetrahedron , vol.59 , pp. 10105-10146
    • Denissova, I.1    Barriault, L.2
  • 47
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    • note
    • Silyl enol ether of α-Me cyclohexanone consists of thermodynamic enolate:kinetic enolate = 87:13.
  • 48
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    • note
    • Silyl enol ether of α-Ph cyclohexanone contains only thermodynamic enolate.


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