Liposome Membranes Assist the L-Proline-catalyzed Aldol Reaction of Acetone and <i>p</i>-Nitrobenzaldehyde in Water

Access this Article

Author(s)

    • Hirose Masanori
    • Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University
    • Fujiwara Shimpei
    • Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University
    • Ishigami Takaaki
    • Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University
    • Suga Keishi
    • Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University
    • Okamoto Yukihiro
    • Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University
    • Umakoshi Hiroshi
    • Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University

Abstract

<p>An <span style="font-variant: small-caps;">l</span>-Proline (<span style="font-variant: small-caps;">l</span>-Pro)-catalyzed aldol reaction of acetone and <i>p</i>-nitrobenzaldehyde (<i>p</i>NBA) occurs in organic solvents such as DMSO, while the presence of excess water inhibits the reaction. Herein, the reaction was carried out in water, in the presence of liposomes. Most liposomes assisted in the conversion of the substrates (conv. >90%). We conclude that the hydrophobic environment of the liposome can be utilized as a reaction medium for this organocatalytic reaction. Although the <span style="font-variant: small-caps;">l</span>-Pro-catalyzed aldol reaction in dimethyl sulfoxide (DMSO) resulted in a high enantiomeric excess of R product (e.e. >70%), the reactions on liposome membranes resulted in e.e. values of 1%.</p>

Journal

  • Chemistry Letters

    Chemistry Letters 47(7), 931-934, 2018

    The Chemical Society of Japan

Codes

  • NII Article ID (NAID)
    130007402750
  • Text Lang
    ENG
  • ISSN
    0366-7022
  • Data Source
    J-STAGE 
Page Top