Nanocellulose enriches enantiomers in asymmetric aldol reactions

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

研究成果: Contribution to journalArticle査読

抄録

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.

本文言語英語
ページ(範囲)37064-37071
ページ数8
ジャーナルRSC Advances
10
61
DOI
出版ステータス出版済み - 10 8 2020

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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