Synthesis of optically active 5-(tert-butyldimethylsiloxy)-2- cyclohexenone and its 6-substituted derivatives as useful chiral building blocks for the synthesis of cyclohexane rings. Synthesis of carvone, penienone, and penihydrone

Journal of the American Chemical Society

Volumn 121, Issue 15, 1999, Pages 3640-3650

  Hareau, Georges P J ^a   Koiwa, Masakazu ^a   Hikichi, Shinichi ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 (TERT BUTYLDIMETHYLSILOXY) 2 CYCLOHEXENONE; CARVONE; CYCLOHEXANE DERIVATIVE; PENIENONE; PENIHYDRONE; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033594345     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9843122     Document Type: Article

References (77)

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37. The conjugate addition of organocuprates onto 5-substituted-2- cyclohexenones yields generally a very high proportion of the trans-adduct; see the following reviews and references therein: Yamamoto, Y. Methoden Org. Chem. (Houben-Weyl), Engl. Ed. 1995, E21b, 2041-2067 (Helmchen, G., Hoffman, R. W., Mulzer, J., Shauman, E., Eds.). Lipshutz, B. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Tokyo, 1991; Vol. 1, pp 107-138. Kozlowski, J. A. Ibid. Vol. 4, pp 169-198. Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135- 631.
38. The conjugate addition of organocuprates onto 5-substituted-2- cyclohexenones yields generally a very high proportion of the trans-adduct; see the following reviews and references therein: Yamamoto, Y. Methoden Org. Chem. (Houben-Weyl), Engl. Ed. 1995, E21b, 2041-2067 (Helmchen, G., Hoffman, R. W., Mulzer, J., Shauman, E., Eds.). Lipshutz, B. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Tokyo, 1991; Vol. 1, pp 107-138. Kozlowski, J. A. Ibid. Vol. 4, pp 169-198. Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135- 631.
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41. 2 (higher-order) indicate that the reagents have been prepared stoichiometrically by mixing CuCN and RLi in the 1:1 and 1:2 ratios, respectively, see: Kronenburg, C. M. P.; Jastrzebski, J. T. B. H.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1998, 120, 9688-9689 and references therein. See also: Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994. The terms "1:1 cyanocuprates" and "1:2 cyanocuprates" are now preferred to "lower-" and "higher-order cyanocuprates" nevertheless, for convenience, we have conserved the old terminology.
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