Highly Stereoselective Synthesis of Trifluoromethylated Compounds via Ester-Enolate [2,3]-Wittig and [3,3]-Ireland-Claisen Rearrangements

Journal of Organic Chemistry

Volumn 62, Issue 1, 1997, Pages 137-150

  Konno, Tsutomu ^a   Umetani, Hideki ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001558946     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961246i     Document Type: Article

References (103)

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71. 3 group have been synthesized from 3,3,3-trifluoropropyne. (a) Drakesmith, F. G.; Stewart, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280. (b) Sibous, L.; Tipping, A. E. J. Fluorine Chem. 1993, 62, 39. (c) Ishihara, T.; Yamasaki, Y.; Ando, T. Tetrahedron Lett. 1985, 26, 79. Burton, D. J.; Yang, Z.-Y.; Morken, P. A. Tetrahedron 1994, 50, 2993. Recently, we have reported the convenient as well as reliable method for the preparation of γ-trifluoromethylated propargylic alcohol.
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80. There have been reported the following reaction conditions, (a) (-78°C, 22 h) Ender, D.; Backhaus, D.; Runsink, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2098. (b) (-70°C, 10 h then → 70 → 0 °C) Takahashi, O.; Mikami, K.; Nakai, T. Chem. Lett. 1987, 69. (c) (-35 1°C, 2 d) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc., Chem. Commun. 1995, 1605. (d) (-78°C, 40 min, then -40°C, 2.7 h) Brückner, R. Chem. Ber. 1989, 122, 703. (e) (-78°C, 2 h) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Synlett 1995, 1035. (f) See ref 21.
81. There have been reported the following reaction conditions, (a) (-78°C, 22 h) Ender, D.; Backhaus, D.; Runsink, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2098. (b) (-70°C, 10 h then → 70 → 0 °C) Takahashi, O.; Mikami, K.; Nakai, T. Chem. Lett. 1987, 69. (c) (-35 1°C, 2 d) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc., Chem. Commun. 1995, 1605. (d) (-78°C, 40 min, then -40°C, 2.7 h) Brückner, R. Chem. Ber. 1989, 122, 703. (e) (-78°C, 2 h) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Synlett 1995, 1035. (f) See ref 21.
82. There have been reported the following reaction conditions, (a) (-78°C, 22 h) Ender, D.; Backhaus, D.; Runsink, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2098. (b) (-70°C, 10 h then → 70 → 0 °C) Takahashi, O.; Mikami, K.; Nakai, T. Chem. Lett. 1987, 69. (c) (-35 1°C, 2 d) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc., Chem. Commun. 1995, 1605. (d) (-78°C, 40 min, then -40°C, 2.7 h) Brückner, R. Chem. Ber. 1989, 122, 703. (e) (-78°C, 2 h) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Synlett 1995, 1035. (f) See ref 21.
83. There have been reported the following reaction conditions, (a) (-78°C, 22 h) Ender, D.; Backhaus, D.; Runsink, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2098. (b) (-70°C, 10 h then → 70 → 0 °C) Takahashi, O.; Mikami, K.; Nakai, T. Chem. Lett. 1987, 69. (c) (-35 1°C, 2 d) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc., Chem. Commun. 1995, 1605. (d) (-78°C, 40 min, then -40°C, 2.7 h) Brückner, R. Chem. Ber. 1989, 122, 703. (e) (-78°C, 2 h) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Synlett 1995, 1035. (f) See ref 21.
84. There have been reported the following reaction conditions, (a) (-78°C, 22 h) Ender, D.; Backhaus, D.; Runsink, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2098. (b) (-70°C, 10 h then → 70 → 0 °C) Takahashi, O.; Mikami, K.; Nakai, T. Chem. Lett. 1987, 69. (c) (-35 1°C, 2 d) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc., Chem. Commun. 1995, 1605. (d) (-78°C, 40 min, then -40°C, 2.7 h) Brückner, R. Chem. Ber. 1989, 122, 703. (e) (-78°C, 2 h) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Synlett 1995, 1035. (f) See ref 21.
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86. 3 substituent. (a) Gassman, P. G.; Harrington, C. K. J. Org. Chem. 1990, 55, 1813. (b) Creary, X.; Sky, A. E.; Mehrsheikh-Mohammadi, M. E. Tetrahedron Lett. 1988, 29, 6839. (c) Yamazaki, T.; Hiraoka, S.; Kitazume, T. J. Org. Chem. 1994, 59, 5100.
87. 3 substituent. (a) Gassman, P. G.; Harrington, C. K. J. Org. Chem. 1990, 55, 1813. (b) Creary, X.; Sky, A. E.; Mehrsheikh-Mohammadi, M. E. Tetrahedron Lett. 1988, 29, 6839. (c) Yamazaki, T.; Hiraoka, S.; Kitazume, T. J. Org. Chem. 1994, 59, 5100.
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98. Koreeda et al. have been reported that the following substrate gave anti isomer in a highly stereoselective fashion. The unusual selectivity has been explained by the envelope-like transition state C suggested by Rautenstrauch (Koreeda, M.; Ricca, D. J. Org. Chem. 1986, 51, 4090.) equiation presented.
99. 3-containing (E)-or (Z)-substrate. It was supposed that HMPA employed as a cosolvent might be a scavenger for lithium cation. Therefore, the transition state without this cation was calculated which is different from Houk's one. As a result, (Z)-substrate affords anti product in a highly stereoselective manner, while (E)-substrate also provides anti isomer stereoselectively. Furthermore, surprisingly, the second stable TS derived from (E)-isomer is the one which might produce anti isomer possessing Z configuration at the newly created olefinic bond.
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