Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Volume 47 , Issue 7
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  • Masanori Hirose, Shimpei Fujiwara, Takaaki Ishigami, Keishi Suga, Yuki ...
    2018 Volume 47 Issue 7 Pages 931-934
    Published: July 05, 2018
    Released: July 05, 2018
    JOURNALS RESTRICTED ACCESS

    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%.

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