Lewis Acid Catalysis in Water with a Hydrophilic Substrate: Scandium-Catalyzed Hydroxymethylation with Aqueous Formaldehyde in Water

Synthesis in deep water: For the title reaction, which proceeds with high selectivities, acid–base interactions between the Sc catalyst and HCHO are important. The reaction was used in the synthesis of an odorant to demonstrate its utility (see scheme; ligand DS not shown; PI‐Pd=polymer‐incarcerated...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 47; no. 36; pp. 6909 - 6911
Main Authors Kokubo, Masaya, Ogawa, Chikako, Kobayashi, Shū
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 25.08.2008
WILEY‐VCH Verlag
Wiley
Subjects
Acids - chemistry
asymmetric catalysis
Catalysis
Chemistry
Chemistry, Multidisciplinary
enolates
Formaldehyde - chemistry
Lewis acids
Methylation
Physical Sciences
Scandium - chemistry
Science & Technology
Silicon Compounds - chemistry
sustainable chemistry
synthetic methods
Water - chemistry
ORGANIC-SYNTHESIS
LIGANDS
ASYMMETRIC ALDOL REACTIONS
COMPLEXES
Lewis acids
MEDIA
enolates
sustainable chemistry
asymmetric catalysis
synthetic methods
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Summary:Synthesis in deep water: For the title reaction, which proceeds with high selectivities, acid–base interactions between the Sc catalyst and HCHO are important. The reaction was used in the synthesis of an odorant to demonstrate its utility (see scheme; ligand DS not shown; PI‐Pd=polymer‐incarcerated palladium; BTF=benzotrifluoride).
Bibliography:ArticleID:ANIE200801849
ark:/67375/WNG-P3LPNVS2-P
Grant-in-Aid for Science Research
This work was partially supported by a Grant-in-Aid for Science Research from the Japan Society for the Promotion of Science (JSPS).
istex:5A1A060B70FDF76713820625A5B667D350E69442
Japan Society for the Promotion of Science
This work was partially supported by a Grant‐in‐Aid for Science Research from the Japan Society for the Promotion of Science (JSPS).
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200801849