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

doi:10.1246/cl.180180

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 journal › Article › peer-review

4 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 language	English
Pages (from-to)	931-934
Number of pages	4
Journal	Chemistry Letters
Volume	47
Issue number	7
DOIs	https://doi.org/10.1246/cl.180180
Publication status	Published - 2018
Externally published	Yes

Keywords

Aldol reaction
Liposome
Organocatalyst

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.180180

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

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%.",

keywords = "Aldol reaction, Liposome, Organocatalyst",

author = "Masanori Hirose and Shimpei Fujiwara and Takaaki Ishigami and Keishi Suga and Yukihiro Okamoto and Hiroshi Umakoshi",

note = "Funding Information: This work was supported by the Funding Program for Next Generation World-Leading Researchers of the Council for Science and Technology Policy (CSTP) (GR066), JSPS Grant-in-Aid for Scientific Research A (26249116), Research Activity Start-up (25889039), Challenging Exploratory Research (T15K142040), and the Sasakawa Scientific Research Grant from The Japan Science Society (29-336). Publisher Copyright: {\textcopyright} 2018 The Chemical Society of Japan.",

year = "2018",

doi = "10.1246/cl.180180",

language = "English",

volume = "47",

pages = "931--934",

journal = "Chemistry Letters",

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publisher = "Chemical Society of Japan",

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TY - JOUR

T1 - Liposome membranes assist the l-proline-catalyzed aldol reaction of acetone and p-nitrobenzaldehyde in water

AU - Hirose, Masanori

AU - Fujiwara, Shimpei

AU - Ishigami, Takaaki

AU - Suga, Keishi

AU - Okamoto, Yukihiro

AU - Umakoshi, Hiroshi

N1 - Funding Information: This work was supported by the Funding Program for Next Generation World-Leading Researchers of the Council for Science and Technology Policy (CSTP) (GR066), JSPS Grant-in-Aid for Scientific Research A (26249116), Research Activity Start-up (25889039), Challenging Exploratory Research (T15K142040), and the Sasakawa Scientific Research Grant from The Japan Science Society (29-336). Publisher Copyright: © 2018 The Chemical Society of Japan.

PY - 2018

Y1 - 2018

N2 - 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%.

AB - 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%.

KW - Aldol reaction

KW - Liposome

KW - Organocatalyst

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DO - 10.1246/cl.180180

M3 - Article

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VL - 47

SP - 931

EP - 934

JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

IS - 7

ER -

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

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Keywords

ASJC Scopus subject areas

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