Stereos elective hydrogenation of D-glucose-derived endo-olefins with a CF3 group -Experimental and theoretical explanations

Heterocycles

Volumn 47, Issue 1, 1998, Pages 129-132

  Hiraoka, Shuichi ^a   Yamazaki, Takashi ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011450214     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s(n)49     Document Type: Article

References (8)

1. T. Yamazaki, S. Hiraoka, and T. Kitazume, Tetrahedron: Asym., 1997, 8, 1157.
2. E. Juaristi and G. Cuevas, Tetrahedron, 1992, 48, 5019.
3. S. Siegel, 'Comprehensive Organic Synthesis,' Vol. 8, ed. by B. M. Trost, Pergamon Press, Inc., New York, 1991, p. 417.
4. E. E. Gonzo and M. Boudart, J. Catal., 1978, 52, 462.
5. Calculations were performed by CACheMOPAC v. 94.10 (MOPAC) implemented in CAChe Worksystem (SONY/Tektronix Corporation).
6. Gaussian 92, Revision G.4, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1992.
7. G. Bott, L. D. Field, and S. Sternhell, J. Am. Chem. Soc., 1980, 102, 5618.
8. Alternatively, olefin isomerization-hydrogenation sequence is also possible. See, ref. 3.