Issue 61, 2020

Nanocellulose enriches enantiomers in asymmetric aldol reactions

Abstract

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 the syn form with a very high yield (99%). Conversely, nanocellulose-free (S)-proline catalysis resulted in poor selectivity (64% ee, syn form) 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.

Graphical abstract: Nanocellulose enriches enantiomers in asymmetric aldol reactions

Supplementary files

Article information

Article type
Paper
Submitted
29 Aug 2020
Accepted
25 Sep 2020
First published
08 Oct 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 37064-37071

Nanocellulose enriches enantiomers in asymmetric aldol reactions

N. J. Ranaivoarimanana, X. Habaki, T. Uto, K. Kanomata, T. Yui and T. Kitaoka, RSC Adv., 2020, 10, 37064 DOI: 10.1039/D0RA07412H

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