Journal
RSC ADVANCES
Volume 10, Issue 61, Pages 37064-37071Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ra07412h
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Funding
- Advanced Low Carbon Technology Research and Development Program from Japan Science and Technology Agency [JPMJAL1505]
- Japan Society for the Promotion of Science [JP18K19233]
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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.
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