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

研究成果: Article査読

3 被引用数 (Scopus)

抄録

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%.

本文言語English
ページ(範囲)931-934
ページ数4
ジャーナルChemistry Letters
47
7
DOI
出版ステータスPublished - 2018
外部発表はい

ASJC Scopus subject areas

  • 化学 (全般)

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