The first generation and stereospecific alkylation of α-trifluoromethyl oxiranyl anion

Organic Letters

Volumn 4, Issue 2, 2002, Pages 173-176

  Yamauchi, Yoshihiro ^a   Katagiri, Toshimasa ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

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ARTICLE;

EID: 0001068290     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016829f     Document Type: Article

References (50)

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40. This optically active TFPO (5-rich, 75% ee) is commercially available from Japan Energy Corporation. For a recent review on preparation and reaction of optically active TFPO, see: (a) Katagiri, T. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999; pp 161. Optically pure (R)- and (S)-TFPO have also been prepared in laboratory scale; see: (b) Von dem Bussche-Hunnefeld, C.; Cescato, C.; Seebach, D. Chem. Ber. 1992, 725, 2795. (c) Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41. (d) Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655. (e) Katagiri, T.; Obara, F. Japan Energy Corp., Jpn. Kokai Tokkyo Koho JP06-247953 1994; Chem. Abstr. 122, 9847b.
41. This optically active TFPO (5-rich, 75% ee) is commercially available from Japan Energy Corporation. For a recent review on preparation and reaction of optically active TFPO, see: (a) Katagiri, T. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999; pp 161. Optically pure (R)- and (S)-TFPO have also been prepared in laboratory scale; see: (b) Von dem Bussche-Hunnefeld, C.; Cescato, C.; Seebach, D. Chem. Ber. 1992, 725, 2795. (c) Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41. (d) Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655. (e) Katagiri, T.; Obara, F. Japan Energy Corp., Jpn. Kokai Tokkyo Koho JP06-247953 1994; Chem. Abstr. 122, 9847b.
42. This optically active TFPO (5-rich, 75% ee) is commercially available from Japan Energy Corporation. For a recent review on preparation and reaction of optically active TFPO, see: (a) Katagiri, T. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999; pp 161. Optically pure (R)- and (S)-TFPO have also been prepared in laboratory scale; see: (b) Von dem Bussche-Hunnefeld, C.; Cescato, C.; Seebach, D. Chem. Ber. 1992, 725, 2795. (c) Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41. (d) Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655. (e) Katagiri, T.; Obara, F. Japan Energy Corp., Jpn. Kokai Tokkyo Koho JP06-247953 1994; Chem. Abstr. 122, 9847b.
43. This optically active TFPO (5-rich, 75% ee) is commercially available from Japan Energy Corporation. For a recent review on preparation and reaction of optically active TFPO, see: (a) Katagiri, T. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999; pp 161. Optically pure (R)- and (S)-TFPO have also been prepared in laboratory scale; see: (b) Von dem Bussche-Hunnefeld, C.; Cescato, C.; Seebach, D. Chem. Ber. 1992, 725, 2795. (c) Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41. (d) Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655. (e) Katagiri, T.; Obara, F. Japan Energy Corp., Jpn. Kokai Tokkyo Koho JP06-247953 1994; Chem. Abstr. 122, 9847b.
44. This optically active TFPO (5-rich, 75% ee) is commercially available from Japan Energy Corporation. For a recent review on preparation and reaction of optically active TFPO, see: (a) Katagiri, T. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999; pp 161. Optically pure (R)- and (S)-TFPO have also been prepared in laboratory scale; see: (b) Von dem Bussche-Hunnefeld, C.; Cescato, C.; Seebach, D. Chem. Ber. 1992, 725, 2795. (c) Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41. (d) Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655. (e) Katagiri, T.; Obara, F. Japan Energy Corp., Jpn. Kokai Tokkyo Koho JP06-247953 1994; Chem. Abstr. 122, 9847b.
45. This optically active TFPO (5-rich, 75% ee) is commercially available from Japan Energy Corporation. For a recent review on preparation and reaction of optically active TFPO, see: (a) Katagiri, T. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999; pp 161. Optically pure (R)- and (S)-TFPO have also been prepared in laboratory scale; see: (b) Von dem Bussche-Hunnefeld, C.; Cescato, C.; Seebach, D. Chem. Ber. 1992, 725, 2795. (c) Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41. (d) Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655. (e) Katagiri, T.; Obara, F. Japan Energy Corp., Jpn. Kokai Tokkyo Koho JP06-247953 1994; Chem. Abstr. 122, 9847b.
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50. Crystallographic data and GIF for compound 4b have been reported as Supporting Information.