Effective Promotion of Proline‐Catalyzed Aldol Reaction in Water by Bile Acid Salt Surfactants

Abstract Proline‐catalyzed aldol reaction of aromatic aldehydes with cyclohexanone was successfully carried out in water without any cosolvent in presence of catalytic amounts of bile acid salt surfactants. The bile acid salts, acting as surfactants, facilitate the dispersion of nonpolar substrates, enabling efficient reaction conditions “in presence of water” which exploit the role of water beyond its simple characteristic as a solvent. While enantioselectivity is moderate, the high yields achieved reflect the potent synergy between proline and sodium deoxycholate (NaDC), underscoring the feasibility of water‐exclusive processes in synthetic organic chemistry.

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Publication Details

Journal
ChemistrySelect
Published
2024-12-01
DOI
https://doi.org/10.1002/slct.202405354
Citations
2
Primary Topic
Chemical Synthesis and Reactions
Type
article
Field-Weighted Citation Impact
0.50

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article

Effective Promotion of Proline‐Catalyzed Aldol Reaction in Water by Bile Acid Salt Surfactants

Fabrizio Vetica, Venanzio Raglione, Luciano Galantini, Jacopo Cautela et al.
2 citations
ChemistrySelect
Chemical Synthesis and Reactions
0.50
article

Effective Promotion of Proline‐Catalyzed Aldol Reaction in Water by Bile Acid Salt Surfactants

Fabrizio Vetica, Venanzio Raglione, Luciano Galantini, Jacopo Cautela, Andrea D’Annibale
article en
2 citations

Abstract

Abstract Proline‐catalyzed aldol reaction of aromatic aldehydes with cyclohexanone was successfully carried out in water without any cosolvent in presence of catalytic amounts of bile acid salt surfactants. The bile acid salts, acting as surfactants, facilitate the dispersion of nonpolar substrates, enabling efficient reaction conditions “in presence of water” which exploit the role of water beyond its simple characteristic as a solvent. While enantioselectivity is moderate, the high yields achieved reflect the potent synergy between proline and sodium deoxycholate (NaDC), underscoring the feasibility of water‐exclusive processes in synthetic organic chemistry.

ChemistrySelectVol. 9(46)
Institute of Structure of Matter (IT), Sapienza University of Rome (IT)
Sapienza Università di Roma
Clean water and sanitation
Openalex Percentile: Top 37%
Chemical Synthesis and Reactions
0.50
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