Pd/C(en)-catalyzed regioselective hydrogenolysis of terminal epoxides to secondary alcohols

Chemical Communications

Volumn , Issue 11, 1999, Pages 1041-1042

  Sajiki, Hironao ^a   Hattori, Kazuyuki ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE; ETHER DERIVATIVE; ETHYLENEDIAMINE DERIVATIVE; GLYCIDOL;

ARTICLE; CATALYSIS; ORGANIC CHEMISTRY;

EID: 0033532534     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902213i     Document Type: Article

References (17)

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2. F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, Part B, Plenum, New York, 1977; M. Bartok and K. L. Lang, The Chemistry of Heterocyclic Compounds - Small Ring Heterocycles, Part 3, ed. A. Weissberger and E. C. Taylor, Wiley, New York, 1985, p. 1 and references therein; R. Sreekumar, R. Padmakumar and P. Rugmini, Tetrahedron Lett., 1998, 39, 5151 and references therein.
3. F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, Part B, Plenum, New York, 1977; M. Bartok and K. L. Lang, The Chemistry of Heterocyclic Compounds - Small Ring Heterocycles, Part 3, ed. A. Weissberger and E. C. Taylor, Wiley, New York, 1985, p. 1 and references therein; R. Sreekumar, R. Padmakumar and P. Rugmini, Tetrahedron Lett., 1998, 39, 5151 and references therein.
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7. Selected reviews: R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, p. 505; M. Hudlicky, Reductions in Organic Chemistry, 2nd edn., ACS, Washington, DC, 1996, p. 113.
8. For examples: M. S. Newman, G. Underwood and M. Renoll, J. Am. Chem. Soc., 1949, 71, 3362; P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, New York, 1979, p. 260; P. N. Rylander, Hydrogenation Methods, Academic Press, New York, 1985, p. 137.
9. For examples: M. S. Newman, G. Underwood and M. Renoll, J. Am. Chem. Soc., 1949, 71, 3362; P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, New York, 1979, p. 260; P. N. Rylander, Hydrogenation Methods, Academic Press, New York, 1985, p. 137.
10. For examples: M. S. Newman, G. Underwood and M. Renoll, J. Am. Chem. Soc., 1949, 71, 3362; P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, New York, 1979, p. 260; P. N. Rylander, Hydrogenation Methods, Academic Press, New York, 1985, p. 137.
11. Besides the catalyst, the substrate also exerts a considerable effect on the regioselectivity (ref. 1 and 4), see also S. Torii, H. Okuno, S. Nakayasu and T. Kotani, Chem. Lett., 1989, 1975.
12. P. S. Dragovic, T. J. Prins and R. Zhou, J. Org. Chem., 1995, 66, 4922.
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14. H. Sajiki, K. Hattori and K. Hirota, J. Org. Chem., 1998, 63, 7990.
15. 2O (20 ml X 2), and dried under a vacuum pump at room temperature for 48 h to give the 10% Pd/ C(en) ( Found: C, 74.10; H, 2.64; N, 3.01%).
16. H. Sajiki, K. Hattori and K. Hirota, J. Chem. Soc., Perkin Trans. 1, 1998, 4043.
17. By use of EtOH instead of MeOH as a solvent, styrene oxide could also be converted to an 87 : 13 mixture of phenethyl alcohol (3R = Ph) and 1-phenylethylene glycol monoethyl ether.