New type of aldol condensations catalyzed by metal(II) complexes of .ALPHA.-amino acid esters and that with cyclodextrin system.

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概要

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• The aldol condensations of <I>p</I>-nitrobenzaldehyde with acetone catalyzed by metal complexes of α-amino acid esters proceeded under mild and neutral conditions to afford an enantiomeric excess aldol-type product, 4-hydroxy-4-(4-nitrophenyl)-2-butanone, along with some dehydrated products without any by-product. The most effective catalyst system was a zinc(II) complex of the tyrosine ethyl ester, Zn<SUP>II</SUP>–(TyrOEt)<SUB>2</SUB> in MeOH. Complexes of the second-row transition metals were inadequate for the reactions. Reactions at 30–40 °C for 24 h were favorable regarding the asymmetric induction. An H<SUB>2</SUB>O solvent was the best for aldol-type product formations without asymmetric induction. An assistant effect of cyclodextrins(especially, β-CD) on the catalysis of the Zn<SUP>II</SUP>–TyrOEt complex were thought to be observed.

• 公益社団法人 日本化学会の論文

著者

• Yamada Yoichi

  Department Of Cellular Physiology And Signal Transduction Sapporo Medical University School Of Medic

• WATANABE Ken-ichi

  Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University

• Goto Katsuhisa

  Department of Chemistry, Faculty of Science, Tokyo Metropolitan University

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