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Volumn 72, Issue 1, 2007, Pages 292-294

Practical stereoselective synthesis of an α-trifluoromethyl-α- alkyl epoxide via a diastereoselective trifluoromethylation reaction

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOMERS; DIASTEREOSELECTIVITY; TRIFLUOROMETHYLATION REACTION;

EID: 33846113396     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061839l     Document Type: Article
Times cited : (38)

References (24)
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    • (1992) Synthetic Fluorine Chemistry
  • 3
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    • Proudfoot, J. R.; Regan, J. R.; Thomson, D. S.; Kuzmich, D.; Lee, T. W.; Hammach, A.; Ralph, M. S.; Zindell, R.; Bekkali, Y. PCT Int. Appl., WO 2004063163 A1 20040729 CAN 141:140466 AN 2004:606445, 2004.
    • (b) Proudfoot, J. R.; Regan, J. R.; Thomson, D. S.; Kuzmich, D.; Lee, T. W.; Hammach, A.; Ralph, M. S.; Zindell, R.; Bekkali, Y. PCT Int. Appl., WO 2004063163 A1 20040729 CAN 141:140466 AN 2004:606445, 2004.
  • 4
    • 33846040630 scopus 로고    scopus 로고
    • Lehmann, M.; Schollkopf, K.; Strehlke, P.; Heinrich, N.; Fritzemeier, K.; Muhn, H.; Krattenmacher, R. (Schering Aktiengesellschaft, Germany), PCT Int. Appl., WO 98-EP3242 19980602 CAN 130: 52321 AN 1998:794993, 1998.
    • (c) Lehmann, M.; Schollkopf, K.; Strehlke, P.; Heinrich, N.; Fritzemeier, K.; Muhn, H.; Krattenmacher, R. (Schering Aktiengesellschaft, Germany), PCT Int. Appl., WO 98-EP3242 19980602 CAN 130: 52321 AN 1998:794993, 1998.
  • 5
    • 33846047773 scopus 로고    scopus 로고
    • Our preliminary account of this study has been documented in a U.S. patent application filed in 2003 PCT publication in 2005, Song, J. J, Tan, Z, Yee, N. K, Senanayake, C. H, Xu, J, Gallou, F, Boehringer Ingelheim Pharmaceuticals, Inc, US 2005209488, A1 20050922
    • Our preliminary account of this study has been documented in a U.S. patent application filed in 2003 (PCT publication in 2005): Song, J. J.; Tan, Z.; Yee, N. K.; Senanayake, C. H.; Xu, J.; Gallou, F. (Boehringer Ingelheim Pharmaceuticals, Inc.), US 2005209488, A1 20050922.
  • 10
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    • Recent examples: (a) Kuko, Y, Yamada, K, Nishizaki, K, Hidaka, T, Mitsubishi Gas Chemical Co, Ltd, Japan, Jpn. Kokai Tokkyo Koho, CODEN: JKXXAF JP 2005023055 A2 20050127 Application: JP 2003-27098.3 20030704, 2005. Priority: CAN 142:155646 AN 2005:72783
    • Recent examples: (a) Kuko, Y.; Yamada, K.; Nishizaki, K.; Hidaka, T. (Mitsubishi Gas Chemical Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho, CODEN: JKXXAF JP 2005023055 A2 20050127 Application: JP 2003-27098.3 20030704, 2005. Priority: CAN 142:155646 AN 2005:72783.
  • 13
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    • For recent reviews, see: a
    • For recent reviews, see: (a) Ma, J.; Cahard, D. Chem. Rev. 2004, 104, 6119.
    • (2004) Chem. Rev , vol.104 , pp. 6119
    • Ma, J.1    Cahard, D.2
  • 24
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    • The absolute stereochemistry of the major diastereomer (10) was confirmed by converting 10 to epoxide 1 and comparison with an authentic sample by chiral HPLC and optical rotation.
    • The absolute stereochemistry of the major diastereomer (10) was confirmed by converting 10 to epoxide 1 and comparison with an authentic sample by chiral HPLC and optical rotation.


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