Nanocellulose enriches enantiomers in asymmetric aldol reactions

Naliharifetra Jessica Ranaivoarimanana, Xin Habaki, Takuya Uto, Kyohei Kanomata, Toshifumi Yui, Takuya Kitaoka

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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 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.

Original languageEnglish
Pages (from-to)37064-37071
Number of pages8
JournalRSC Advances
Volume10
Issue number61
DOIs
Publication statusPublished - Oct 8 2020

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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