Combined proline-surfactant organocatalyst for the highly diastereo- and enantioselective aqueous direct cross-aldol reaction of aldehydes

Yujiro Hayashi; Seiji Aratake; Tsubasa Okano; Junichi Takahashi; Tatsunobu Sumiya; Mitsuru Shoji

doi:10.1002/anie.200601156

Combined proline-surfactant organocatalyst for the highly diastereo- and enantioselective aqueous direct cross-aldol reaction of aldehydes

Yujiro Hayashi, Seiji Aratake, Tsubasa Okano, Junichi Takahashi, Tatsunobu Sumiya, Mitsuru Shoji

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

182 Citations (Scopus)

Abstract

(Chemical Equation Presented) Why not combine the two? The asymmetric direct aldol reaction of two different aldehydes was catalyzed by a combined proline-surfactant organic catalyst in the presence of water. A stable emulsion was formed in the reaction mixture, and the aldols were obtained with excellent diastereo- and enantioselectivities (see scheme).

Original language	English
Pages (from-to)	5527-5529
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	33
DOIs	https://doi.org/10.1002/anie.200601156
Publication status	Published - 2006 Aug 18

Keywords

Aldol reaction
Asymmetric synthesis
Green chemistry
Organocatalysis
Surfactants

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200601156

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abstract = "(Chemical Equation Presented) Why not combine the two? The asymmetric direct aldol reaction of two different aldehydes was catalyzed by a combined proline-surfactant organic catalyst in the presence of water. A stable emulsion was formed in the reaction mixture, and the aldols were obtained with excellent diastereo- and enantioselectivities (see scheme).",

keywords = "Aldol reaction, Asymmetric synthesis, Green chemistry, Organocatalysis, Surfactants",

author = "Yujiro Hayashi and Seiji Aratake and Tsubasa Okano and Junichi Takahashi and Tatsunobu Sumiya and Mitsuru Shoji",

year = "2006",

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language = "English",

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T1 - Combined proline-surfactant organocatalyst for the highly diastereo- and enantioselective aqueous direct cross-aldol reaction of aldehydes

AU - Hayashi, Yujiro

AU - Aratake, Seiji

AU - Okano, Tsubasa

AU - Takahashi, Junichi

AU - Sumiya, Tatsunobu

AU - Shoji, Mitsuru

PY - 2006/8/18

Y1 - 2006/8/18

N2 - (Chemical Equation Presented) Why not combine the two? The asymmetric direct aldol reaction of two different aldehydes was catalyzed by a combined proline-surfactant organic catalyst in the presence of water. A stable emulsion was formed in the reaction mixture, and the aldols were obtained with excellent diastereo- and enantioselectivities (see scheme).

AB - (Chemical Equation Presented) Why not combine the two? The asymmetric direct aldol reaction of two different aldehydes was catalyzed by a combined proline-surfactant organic catalyst in the presence of water. A stable emulsion was formed in the reaction mixture, and the aldols were obtained with excellent diastereo- and enantioselectivities (see scheme).

KW - Aldol reaction

KW - Asymmetric synthesis

KW - Green chemistry

KW - Organocatalysis

KW - Surfactants

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 33

ER -

Combined proline-surfactant organocatalyst for the highly diastereo- and enantioselective aqueous direct cross-aldol reaction of aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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