Inversion of stereoselectivity by hydrophobic interligand interactions. Preparation, structure, and stereoselectivity of {N,N'-ethylenebis(1,1,1-trifluoro-4-amino-2-pentanonato)}(L-amino acidato)cobalt(III).

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概要

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• Ternary cobalt(III) complexes with a general formula β<SUB>2</SUB>-[Co(tfac<SUB>2</SUB>en)(L-aa)], where tfac<SUB>2</SUB>en is the titled Schiff base ligand and L-aa denotes L-ala, L-leu, L-phe, L-tyr, and L-trp, were synthesized and separated into two diastereoisomers. On the bases of X-ray crystal analysis of the L-phe complex, CD, and <SUP>1</SUP>H and <SUP>19</SUP>F NMR spectra, the structure of (−)<SUB>435</SUB>- and (+)<SUB>435</SUB>-isomers was determined to be <I>Λ</I>- and <I>Δ</I>-cis-β<SUB>2</SUB>-forms, respectively, and preferred conformation of the coordinated L-amino acidates was assummed to be <I>h</I>-form in solution. All the complexes showed stereoselectivity for the <I>Λ</I>-isomer in acetone and methanol, but the selectivity decreased or reversed with addition of water. The solvent-dependent stereoselectivity was explained in terms of steric repulsion and hydrophobic interligand interactions between CF<SUB>3</SUB> group of tfac<SUB>2</SUB>en and side chain of L-aa.

• 公益社団法人 日本化学会の論文

著者

• Fujii Yuki

  Department Of Chemistry Faculty Of Science Ibaraki University

• Kida Shigeo

  Institute for Molecular Science

• Konishi Yoshie

  Department of Chemistry, Ibaraki University

• Shinohara Homare

  Department of Chemistry, Ibaraki University

• Mikuriya Masahiro

  Institute for Molecular Science

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