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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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Communication
Lewis Acid Catalysis in Water with a Hydrophilic Substrate: Scandium-Catalyzed Hydroxymethylation with Aqueous Formaldehyde in Water†
Article first published online: 29 JUL 2008
DOI: 10.1002/anie.200801849
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Kokubo, M., Ogawa, C. and Kobayashi, S. (2008), Lewis Acid Catalysis in Water with a Hydrophilic Substrate: Scandium-Catalyzed Hydroxymethylation with Aqueous Formaldehyde in Water. Angew. Chem. Int. Ed., 47: 6909–6911. doi: 10.1002/anie.200801849
- †
Publication History
- Issue published online: 20 AUG 2008
- Article first published online: 29 JUL 2008
- Manuscript Revised: 9 JUN 2008
- Manuscript Received: 21 APR 2008
Funded by
- Grant-in-Aid for Science Research
- Japan Society for the Promotion of Science
Keywords:
- asymmetric catalysis;
- enolates;
- Lewis acids;
- sustainable chemistry;
- synthetic methods
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).