A new access to β-methyl substituted secondary alcohols. Application to the synthesis of 4-methylheptan-3-ol

Tetrahedron Asymmetry

Volumn 10, Issue 18, 1999, Pages 3521-3528

  Růžička, Josef ^a   Koutek, Bohumír ^b   Streinz, Ludvík ^b   Šaman, David ^b   Lešetický, Ladislav ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE;

ARTICLE; DESULFURIZATION; HYDROLYSIS; OPTICAL RESOLUTION; PRIORITY JOURNAL; REDUCTION; STEREOISOMERISM; SYNTHESIS;

EID: 0038532595     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00372-9     Document Type: Article

References (25)

1. For selected reviews, see: Mori, K. Tetrahedron 1989, 45, 3233; Mori, K. In The Total Synthesis of Natural Products, Vol. 9; ApSimon, J. W., Ed.; Wiley: New York, 1992; pp. 1-534; Mori, K. In Advances in Asymmetric Synthesis, Vol. 1; Hassmer, A., Ed.; JAI Press: Greenwich, 1995; pp. 211-269; Mori, K. Eur. J. Org. Chem. 1998, 1479; Koutek, B.; Streinz, L.; Romaňuk, M. Collect. Czech. Chem. Commun. 1998, 63, 899.
2. For selected reviews, see: Mori, K. Tetrahedron 1989, 45, 3233; Mori, K. In The Total Synthesis of Natural Products, Vol. 9; ApSimon, J. W., Ed.; Wiley: New York, 1992; pp. 1-534; Mori, K. In Advances in Asymmetric Synthesis, Vol. 1; Hassmer, A., Ed.; JAI Press: Greenwich, 1995; pp. 211-269; Mori, K. Eur. J. Org. Chem. 1998, 1479; Koutek, B.; Streinz, L.; Romaňuk, M. Collect. Czech. Chem. Commun. 1998, 63, 899.
3. For selected reviews, see: Mori, K. Tetrahedron 1989, 45, 3233; Mori, K. In The Total Synthesis of Natural Products, Vol. 9; ApSimon, J. W., Ed.; Wiley: New York, 1992; pp. 1-534; Mori, K. In Advances in Asymmetric Synthesis, Vol. 1; Hassmer, A., Ed.; JAI Press: Greenwich, 1995; pp. 211-269; Mori, K. Eur. J. Org. Chem. 1998, 1479; Koutek, B.; Streinz, L.; Romaňuk, M. Collect. Czech. Chem. Commun. 1998, 63, 899.
4. For selected reviews, see: Mori, K. Tetrahedron 1989, 45, 3233; Mori, K. In The Total Synthesis of Natural Products, Vol. 9; ApSimon, J. W., Ed.; Wiley: New York, 1992; pp. 1-534; Mori, K. In Advances in Asymmetric Synthesis, Vol. 1; Hassmer, A., Ed.; JAI Press: Greenwich, 1995; pp. 211-269; Mori, K. Eur. J. Org. Chem. 1998, 1479; Koutek, B.; Streinz, L.; Romaňuk, M. Collect. Czech. Chem. Commun. 1998, 63, 899.
5. For selected reviews, see: Mori, K. Tetrahedron 1989, 45, 3233; Mori, K. In The Total Synthesis of Natural Products, Vol. 9; ApSimon, J. W., Ed.; Wiley: New York, 1992; pp. 1-534; Mori, K. In Advances in Asymmetric Synthesis, Vol. 1; Hassmer, A., Ed.; JAI Press: Greenwich, 1995; pp. 211-269; Mori, K. Eur. J. Org. Chem. 1998, 1479; Koutek, B.; Streinz, L.; Romaňuk, M. Collect. Czech. Chem. Commun. 1998, 63, 899.
6. For selected reviews, see: Kuthan, J.; Šebek, P.; Bohm S. In Advances in Heterocyclic Chemistry, Vol. 59; Katritzky, A. R., Ed.; Academic Press: San Diego: 1994, p. 179; Vedejs, E.; Kraft, G. A. Tetrahedron 1982, 38, 2857; see also: Ward, D. E.; Gai, Y.; Lai, Y. Synlett 1996, 261.
7. For selected reviews, see: Kuthan, J.; Šebek, P.; Bohm S. In Advances in Heterocyclic Chemistry, Vol. 59; Katritzky, A. R., Ed.; Academic Press: San Diego: 1994, p. 179; Vedejs, E.; Kraft, G. A. Tetrahedron 1982, 38, 2857; see also: Ward, D. E.; Gai, Y.; Lai, Y. Synlett 1996, 261.
8. For selected reviews, see: Kuthan, J.; Šebek, P.; Bohm S. In Advances in Heterocyclic Chemistry, Vol. 59; Katritzky, A. R., Ed.; Academic Press: San Diego: 1994, p. 179; Vedejs, E.; Kraft, G. A. Tetrahedron 1982, 38, 2857; see also: Ward, D. E.; Gai, Y.; Lai, Y. Synlett 1996, 261.
9. Streinz, L.; Svatoš, A.; Vrkoč, J.; Meinwald, J. J. Chem. Soc., Perkin Trans. 1 1994, 3509.
10. Růžička, J.; Streinz, L.; Rejzek, M.; Wimmer, Z.; Zarevúcka, M.; Koutek, B.; Lešetický, L. J. Chem. Res. (M) 1998, 3401.
11. Attygale, A. B.; Vostrowsky, O.; Bestmann, H. J.; Steghaus-Kovac, S.; Maschwitz, U. Naturwissenschaften 1988, 75, 315.
12. Pearce, G. T.; Gore, W. E.; Silverstein, W. E.; Peacock, J. W.; Cuthbert, R. A.; Lanier, G. N.; Simeone, J. B. J. Chem. Ecol. 1975, 1, 115.
13. See Ref. 1 for more details.
14. Blight, M. M.; Henderson, N. C.; Wadhams, L. J. Insect Biochem. 1983, 13, 27.
15. Tripathy, P. B.; Matteson, D. S. Synthesis 1990, 200.
16. Unelius, R. C.; Sandell, J.; Orrenius, C. Collect. Czech. Chem. Commun. 1998, 63, 525.
17. Takemura, T.; Jones, J. B. J. Org. Chem. 1983, 48, 791.
18. Matsuyama, H.; Takei, Y.; Kobayashi, M. Bull. Chem. Soc. Jpn. 1986, 59, 2657.
19. Matsuyama, H.; Miyzawa, Y.; Takei, Y.; Kobayashi, M. J. Org. Chem. 1987, 52, 1703.
20. Matsuyama, H.; Fujii, S.; Nakamura, Y.; Kikuchi K.; Ikemoto, I.; Kamigata, N. Bull. Chem. Soc. Jpn. 1993, 66, 1743.
21. Young, J. A.; Tarrant, P. J. Am. Chem. Soc. 1949, 71, 2432; Pearson, D. L., Ph.D. Thesis, The Synthesis of Enantiomerically Pure Inhalation Anesthetics - Halothane and Enflurane, Cornell University, 1990.
22. Young, J. A.; Tarrant, P. J. Am. Chem. Soc. 1949, 71, 2432; Pearson, D. L., Ph.D. Thesis, The Synthesis of Enantiomerically Pure Inhalation Anesthetics - Halothane and Enflurane, Cornell University, 1990.
23. Hoffmann, W.; Ladner, W.; Heibig, W. Liebigs Annalen 1984, 1170.
24. Fehnel, E. A.; Carmack, M. J. Am. Chem. Soc. 1948, 70, 1813.
25. Mori, K. Tetrahedron 1977, 33, 289.