Sparteine Thiourea: The Synthesis of an N Chiral Bispidine-Quinolizidine-Derived Organocatalyst and Applications in Asymmetric Synthesis of Dihydropyrano[


Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
07 May 2024
Historique:
medline: 7 5 2024
pubmed: 7 5 2024
entrez: 7 5 2024
Statut: aheadofprint

Résumé

Bispidine, a bridged bicyclic diamine, has been widely utilized as a rigid scaffold in chiral chelating ligands in asymmetric synthesis. In particular, a chiral bispidine-quinolizidine hybrid, such as sparteine, was utilized in asymmetric synthesis involving a metal, exhibiting superior catalytic activity. In this study, we report the design and synthesis of a series of sparteine-derived organocatalysts and the utilization of these catalysts in tandem Michael addition-cyclization reactions. These catalysts have shown excellent catalytic reactivity and enantioselectivity, and the corresponding dihydropyrano[

Identifiants

pubmed: 38712792
doi: 10.1021/acs.joc.4c00638
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Auteurs

Hexin Sun (H)

School of Pharmaceutical Science and Technology (SPST), Faculty of Medicine, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. China.
International Joint Research Centre for Molecular Sciences, Tianjin University, Tianjin 300072, China.
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. China.

Lin Huang (L)

School of Pharmaceutical Science and Technology (SPST), Faculty of Medicine, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. China.
International Joint Research Centre for Molecular Sciences, Tianjin University, Tianjin 300072, China.
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. China.

Jianhui Huang (J)

School of Pharmaceutical Science and Technology (SPST), Faculty of Medicine, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. China.
International Joint Research Centre for Molecular Sciences, Tianjin University, Tianjin 300072, China.
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. China.

Classifications MeSH