A practical transformation of aldehydes into (E)-iodoalkenes with geminal dichromium reagents

Synlett

Volumn , Issue 8, 1999, Pages 1268-1270

  Takai, Kazuhiko ^a   Ichiguchi, Tetsuya ^a   Hikasa, Shintaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Chromium(II); Geminal dichromium reagent; Iodoform, (E) 1 iodoalkene; Zinc

Indexed keywords

ALDEHYDE DERIVATIVE; ALUMINUM; CHROMIUM DERIVATIVE; DIOXANE; IRON; MAGNESIUM; MANGANESE; ORGANOIODINE DERIVATIVE; SODIUM IODIDE; TRIMETHYLSILYL DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032769892     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2829     Document Type: Article

References (16)

1. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
2. For some representative application to total synthesis, see: Nicolaou, K. C.; Bertinato, P.; Piscopio, A. D.; Chakraborty, T. K.; Minowa, N. J. Chem. Soc., Chem. Commun. 1993, 619. Kanda, Y.; Fukuyama, T. J. Am. Chem. Soc. 1993, 115, 8451. Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. See also ref. 7.
3. For some representative application to total synthesis, see: Nicolaou, K. C.; Bertinato, P.; Piscopio, A. D.; Chakraborty, T. K.; Minowa, N. J. Chem. Soc., Chem. Commun. 1993, 619. Kanda, Y.; Fukuyama, T. J. Am. Chem. Soc. 1993, 115, 8451. Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. See also ref. 7.
4. For some representative application to total synthesis, see: Nicolaou, K. C.; Bertinato, P.; Piscopio, A. D.; Chakraborty, T. K.; Minowa, N. J. Chem. Soc., Chem. Commun. 1993, 619. Kanda, Y.; Fukuyama, T. J. Am. Chem. Soc. 1993, 115, 8451. Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. See also ref. 7.
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8. Chromium(II) chloride (99.9% purity) was purchased from Aldrich Chemical Co. Zinc powder (99.9% purity) was purchased from Merck Co. and activated by washing with IM hydrochloric acid, water, methanol, and ether, and dried in vacuo.
9. Sodium iodide was dried at 120 °C (2 Torr) for 1 day. Morita, T.; Okamoto, Y.; Sakurai, H. J. Chem, Soc., Chem. Commun. 1978, 874. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. Synthesis 1979, 61. See also, ref. 4.
10. Sodium iodide was dried at 120 °C (2 Torr) for 1 day. Morita, T.; Okamoto, Y.; Sakurai, H. J. Chem, Soc., Chem. Commun. 1978, 874. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. Synthesis 1979, 61. See also, ref. 4.
11. Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497. In contrast to the stoichiometric reaction in dioxane where the reaction did not complete after 4 days, the catalytic process completed within 4 h in the solvent.
12. Okazoe, T.; Takai, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 951; Takai, K.; Kataoka, Y.; Okazoe, T.; Utimoto, K. Tetrahedron Lett. 1987, 28, 1443; Takai, K.; Shinomiya, N.; Kaihara, H.; Yoshida, N.; Moriwake, T.; Utimoto, K. Synlett 1995, 963.
13. Okazoe, T.; Takai, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 951; Takai, K.; Kataoka, Y.; Okazoe, T.; Utimoto, K. Tetrahedron Lett. 1987, 28, 1443; Takai, K.; Shinomiya, N.; Kaihara, H.; Yoshida, N.; Moriwake, T.; Utimoto, K. Synlett 1995, 963.
14. Okazoe, T.; Takai, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 951; Takai, K.; Kataoka, Y.; Okazoe, T.; Utimoto, K. Tetrahedron Lett. 1987, 28, 1443; Takai, K.; Shinomiya, N.; Kaihara, H.; Yoshida, N.; Moriwake, T.; Utimoto, K. Synlett 1995, 963.
15. Chromium(III) hexahydrate (99.995% purity) was purchased from Aldrich Chemical Co. and dehydrated by treatment with thionyl chloride. Pray, A. R. Inorg. Synth. 1954, 5, 153. Chromium(III) chloride THF complex (97% purity) was purchased from Aldrich Chemical Co.
16. 1 i}M/f/rl999, No. 8, 1271-1273