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Nanocellulose enriches enantiomers in asymmetric aldol reactions

RSC advances, 2020-10, Vol.1 (61), p.3764-3771 [Peer Reviewed Journal]

This journal is © The Royal Society of Chemistry. ;Copyright Royal Society of Chemistry 2020 ;This journal is © The Royal Society of Chemistry 2020 The Royal Society of Chemistry ;ISSN: 2046-2069 ;EISSN: 2046-2069 ;DOI: 10.1039/d0ra07412h ;PMID: 35521245

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  • Title:
    Nanocellulose enriches enantiomers in asymmetric aldol reactions
  • Author: Ranaivoarimanana, Naliharifetra Jessica ; Habaki, Xin ; Uto, Takuya ; Kanomata, Kyohei ; Yui, Toshifumi ; Kitaoka, Takuya
  • Subjects: Aldehydes ; Asymmetry ; Catalysis ; Cellulose ; Chemical synthesis ; Chemistry ; Enantiomers ; Nanofibers ; Oxidation ; Proline ; Selectivity ; Solid surfaces ; Wood pulp
  • Is Part Of: RSC advances, 2020-10, Vol.1 (61), p.3764-3771
  • Description: 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. Catalytically inactive cellulose nanofibers with crystalline solid surfaces enhance highly enantioselective organocatalysis at the interface in proline-mediated aldol reactions.
  • Publisher: England: Royal Society of Chemistry
  • Language: English
  • Identifier: ISSN: 2046-2069
    EISSN: 2046-2069
    DOI: 10.1039/d0ra07412h
    PMID: 35521245
  • Source: PubMed Central
    DOAJ Directory of Open Access Journals
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