Inositols as chiral templates: 1,4-conjugate addition to tethered cinnamic esters

Organic and Biomolecular Chemistry

Volumn 2, Issue 16, 2004, Pages 2272-2274

  Cousins, Ghislaine ^a   Falshaw, Andrew ^b   Hoberg, John O ^c  

^a VICTORIA UNIVERSITY OF WELLINGTON   (New Zealand)

^b CALLAGHAN INNOVATION   (New Zealand)

^c UNIVERSITY OF WYOMING   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; ESTERIFICATION; HYDROLYSIS; HYDROXYLATION; MIXTURES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CHIRAL TEMPLATES; CINNAMIC ESTERS; INOSITOLS; ORGANIC SYNTHESIS;

ESTERS;

CINNAMIC ACID DERIVATIVE; COPPER; ESTER; INOSITOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROLYSIS; STEREOISOMERISM;

CINNAMATES; COPPER; ESTERS; HYDROLYSIS; INOSITOL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 4644313619     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b408467e     Document Type: Article

References (15)

1. M. Nogradi, Stereoselective Synthesis, VCH Publishers, New York, 1995.
2. J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley Interscience, New York, 1995.
3. A. K. Ghosh, P. Mathivanan and J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1.
4. J. K. Whitesell, Chem. Rev., 1989, 89, 1581.
5. G. F. Painter and A. J. Falshaw, J. Chem. Soc., Perktn Trans 1, 2000, 1157.
6. T. Akiyama, M. Hara, K. Fuchibe, S. Sakamoto and K. Yamaguchi, Chem. Commun., 2003, 1734.
7. J. J. Kiddle, Chem. Rev., 1995, 95, 2189.
8. K. Totani, T. Nagatsuka, S. Yanaguchi, K. Takao, S. Ohba and J. Tadano, J. Org. Chem., 2001, 66, 5965.
9. J. Larner, J. D. Price, D. Heimark, L. Smith, G. Rule, T. Piccariello, M. C. Fonteles, C. Pontes, D. Vale and L. Huang, J. Med. Chem., 2003, 46, 3283.
10. G. Cousins, A. Falshaw and J. O. Hoberg, Carbohydr. Res., 2003, 338, 995.
11. P. A. Clarke, N. E. Kayaleh, M. A. Smith, J. R. Baker, S. J. Bird and C. Chan, J. Org. Chem., 2002, 67, 5226.
12. P. A. Clarke, R. A. Holton and N. E. Kayaleh, Tetrahedron Lett., 2000, 41, 2687.
13. 4 reduction of 8a; and comparison of 11a to literature values (see ESI†)All other compounds were established by comparison of NMR data to 8a or 8c and 10a or 10c.
14. R. J. Loncharich, T. R. Schwartz and K. N. Houk, J. Am. Chem. Soc., 1987, 109, 14.
15. W. Oppolzer, Angew. Chem., Int. Ed. Engl., 1984, 23, 876.