Rhodium-catalyzed asymmetric 1,4-addition of aryltitanium reagents generating chiral titanium enolates: Isolation as silyl enol ethers

Journal of the American Chemical Society

Volumn 124, Issue 41, 2002, Pages 12102-12103

  Hayashi, Tamio ^a   Tokunaga, Norihito ^a   Yoshida, Kazuhiro ^a   Han, Jin Wook ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; RHODIUM; SILANE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 0037120913     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027663w     Document Type: Article

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29. As recent examples of the copper-catalyzed asymmetric 1,4-addition of organozinc reagents generating zinc enolates: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262. (c) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
30. As recent examples of the copper-catalyzed asymmetric 1,4-addition of organozinc reagents generating zinc enolates: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262. (c) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
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34. For reviews on organotitanium reagents: (a) Duthaler, R. O.; Hafner, A. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, p 447. (b) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Verlag: 1986. (c) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (d) Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Schreiber, S. L., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, p 139.
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36. For reviews on organotitanium reagents: (a) Duthaler, R. O.; Hafner, A. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, p 447. (b) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Verlag: 1986. (c) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (d) Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Schreiber, S. L., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, p 139.
37. 8): δ 1.27 (br d, J = 5.5 Hz, 18H), 1.37-1.49 (br m, 1H), 1.60-1.72 (br m, 1H), 1.74-1,86 (br m, 1H), 1.86-2.00 (br m, 1H), 2.14-2.43 (br m, 2H), 3.47-3.58 (br m, 1H), 4.38-4.75 (br m, 3H), 4.91-5.11 (br m, 1H), 7.11 (t, J = 7.2 Hz, 1H), 7.21 (t, J = 7.2 Hz, 2H), 7.25 (d, J = 7.2 Hz, 2H).
38. 3 has been reported: Reetz, M. T.; Peter, R. Tetrahedron Lett. 1981, 22, 4691. (b) For a review on titanium enolates: Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 301.
39. 3 has been reported: Reetz, M. T.; Peter, R. Tetrahedron Lett. 1981, 22, 4691. (b) For a review on titanium enolates: Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 301.
40. 4: Yachi, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 1999, 121, 9465. See also. Han, Z.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 2000, 41, 4415.
41. 4: Yachi, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 1999, 121, 9465. See also. Han, Z.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 2000, 41, 4415.
42. Copper-catalyzed 1,4-addition of organotitanium reagents in the presence of chlorotrimethylsilane giving silyl enol ethers has been reported: Arai, M.; Lipshutz, B. H.; Nakamura, E. Tetrahedron 1992, 48, 5709.
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47. Contaminated with ca. 8% of its isomer.
48. The (oxa-π-allyl)rhodium complex 8 was generated in the NMR sample tube by addition of 2-cyclohexenone to phenylrhodium 9 (ref 7).