Oct 8, 2020
Nanocellulose enriches enantiomers in asymmetric aldol reactions
RSC Advances
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- Volume
- 10
- Number
- 61
- First page
- 37064
- Last page
- 37071
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1039/d0ra07412h
© The Royal Society of Chemistry 2020. Cellulose nanofibers obtained from wood pulp by TEMPO-mediated oxidation acted as a chiral enhancer in direct aldol reactions of 4-nitrobenzaldehyde and cyclopentanone with (S)-proline as an organocatalyst. Surprisingly, catalytically inactive TEMPO-oxidized cellulose nanofibers enriched the (R,R)-enantiomer in this reaction, affording 89% ee in thesynform with a very high yield (99%). Conversely, nanocellulose-free (S)-proline catalysis resulted in poor selectivity (64% ee,synform) with a low yield (18%). Green organocatalysis occurring on nanocellulose solid surfaces bearing regularly aligned chiral carbons on hydrophobic crystalline facets will provide new insight into asymmetric synthesis strategies for interfacial catalysis.
- Link information
- ID information
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- DOI : 10.1039/d0ra07412h
- eISSN : 2046-2069
- SCOPUS ID : 85093866033