Liposome membranes assist the l-proline-catalyzed aldol reaction of acetone and p-nitrobenzaldehyde in water

Masanori Hirose, Shimpei Fujiwara, Takaaki Ishigami, Keishi Suga, Yukihiro Okamoto, Hiroshi Umakoshi

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

An L-Proline (L-Pro)-catalyzed aldol reaction of acetone and p-nitrobenzaldehyde (pNBA) 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 L-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%.

Original languageEnglish
Pages (from-to)931-934
Number of pages4
JournalChemistry Letters
Volume47
Issue number7
DOIs
Publication statusPublished - 2018
Externally publishedYes

Keywords

  • Aldol reaction
  • Liposome
  • Organocatalyst

ASJC Scopus subject areas

  • Chemistry(all)

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