Organocatalytic atroposelective synthesis of naphthoquinone thioglycosides from aryl-naphthoquinones and thiosugars.

Thiosugars Naphthoquinones Thioglycosides

Journal

Chemical communications (Cambridge, England)
ISSN: 1364-548X
Titre abrégé: Chem Commun (Camb)
Pays: England
ID NLM: 9610838

Informations de publication

Date de publication:
08 Jun 2023
Historique:
medline: 12 6 2023
pubmed: 25 5 2023
entrez: 25 5 2023
Statut: epublish

Résumé

In this study, we report an organocatalytic formal coupling strategy for aryl-naphthoquinones with thiosugars that provides straightforward access to the axially chiral naphthoquinone thioglycoside with excellent stereoselectivity. Mechanistic studies revealed the key role of H-bonding in stereochemical recognition. The reaction pathway involves the atroposelective addition, followed by stereoretentive oxidation of the hydroquinone intermediate.

Identifiants

DOI: 10.1039/d3cc01705b PMID: 37227142
pubmed: 37227142
doi: 10.1039/d3cc01705b
doi:

Substances chimiques

Thiosugars 0
Naphthoquinones 0
Thioglycosides 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

7279-7282

Auteurs

Yuling Wu (Y)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.

Wu-Jingyun Zhou (WJ)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.

Laiping Yao (L)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.

Yadi Niu (Y)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.

Hongli Zhao (H)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.

Cheng Peng (C)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.
ORCID: 0000-0003-3303-906X

Bo Han (B)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.
ORCID: 0000-0003-3200-4682

Wei Huang (W)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.
ORCID: 0000-0003-0832-1864

Gu Zhan (G)

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China. haungwei@cdutcm.edu.cn.
ORCID: 0000-0002-5263-8263

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Classifications MeSH

questionsmedicales.fr › Glucides › Thiosucres › Organocatalytic atroposelective synthesis of...
questionsmedicales.fr › Composés polycycliques › Hydrocarbures aromatiques polycycliques › Naphtalènes › Naphtoquinones › Organocatalytic atroposelective synthesis of...
questionsmedicales.fr › Glucides › Hétérosides › Thioglycosides › Organocatalytic atroposelective synthesis of...