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

Research output: Contribution to journalArticle

252 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 languageEnglish
Pages (from-to)5527-5529
Number of pages3
JournalAngewandte Chemie - International Edition
Volume45
Issue number33
DOIs
Publication statusPublished - 2006 Aug 18
Externally publishedYes

Fingerprint

Enantioselectivity
Aldehydes
Proline
Surface-Active Agents
Emulsions
Surface active agents
Catalysts
Water
3-hydroxybutanal

Keywords

  • Aldol reaction
  • Asymmetric synthesis
  • Green chemistry
  • Organocatalysis
  • Surfactants

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Combined proline-surfactant organocatalyst for the highly diastereo- and enantioselective aqueous direct cross-aldol reaction of aldehydes. / Hayashi, Yujiro; Aratake, Seiji; Okano, Tsubasa; Takahashi, Junichi; Sumiya, Tatsunobu; Shoji, Mitsuru.

In: Angewandte Chemie - International Edition, Vol. 45, No. 33, 18.08.2006, p. 5527-5529.

Research output: Contribution to journalArticle

Hayashi, Yujiro ; Aratake, Seiji ; Okano, Tsubasa ; Takahashi, Junichi ; Sumiya, Tatsunobu ; Shoji, Mitsuru. / Combined proline-surfactant organocatalyst for the highly diastereo- and enantioselective aqueous direct cross-aldol reaction of aldehydes. In: Angewandte Chemie - International Edition. 2006 ; Vol. 45, No. 33. pp. 5527-5529.
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AU - Sumiya, Tatsunobu

AU - Shoji, Mitsuru

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