topbannblueonwhite (7K)

Research:

Inositol-diamine-based ligands

Having developed syntheses of optically pure inositols as part of other research projects in our laboratory, we became interested in possible applications of such compounds to problems in synthetic organic chemistry. It has long been known that optically active amine-based ligands, especially those derived from cyclohexane diamines,[1] can be very valuable platforms for metal-catalyzed enantioselective reactions. We decided to examine if inositol-diamine-based ligands could be useful for these reactions.

ligand project_b (2K)

We prepared bis-pyridyl ligand 1[2] from the corresponding inositol-diamine that was in turn prepared from tetrabenzyl-myo-inositol. We are interested in determining if transition metal complexes of this or related ligands might be useful as catalysts for enantioselective reactions. Preliminary work[3] with the Mn(II) and Fe (II) complex of 1 has been disappointing because the complexes appear to be a poor catalysts for olefin epoxidation, but catalysis of other reactions, complexation with other metals, and use of modified ligands have yet to be explored.

References

1.

E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker, and L. Deng J. Am. Chem. Soc. 1991, 113, 7063-4.

2.

V. N. Azev and M. d'Alarcao J. Org. Chem. 2004, 69, 4839. Link to PDF.

2.

S. Taktak, E.V. Rybak-Akimova, unpublished results.


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Tufts University