AI Article Synopsis
- A new homodinuclear Co2/aminophenol sulfonamide complex has been created for the asymmetric Michael reaction, showing high efficiency with β-ketoesters and nitroolefins.
- The reaction demonstrates excellent results, achieving up to 99% yield and high enantioselectivity, remaining effective even on a larger 50 mmol scale.
- Mechanistic studies suggest that the Co2/2a complex is the active species driving the catalysis, leading to a proposed catalytic cycle.
Article Abstract
A homodinuclear Co2/aminophenol sulfonamide complex has been developed for the asymmetric Michael reaction of β-ketoesters with nitroolefins. This procedure is capable of tolerating a wide range of substrates and excellent results (up to 99% yield, >99 : 1 dr and 98% ee) can also be obtained. Moreover, the reaction could be carried out on a 50 mmol scale without any decrease in the enantioselectivity and reactivity. On the basis of the results of mechanistic studies, we proposed that the Co2/2a complex would be the active species and a possible catalytic cycle was described.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8ob00773j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Surgical resection of a solitary fibrous tumour causing refractory hypoglycaemia: Doege-Potter syndrome.
BMJ Case Rep
January 2025
Department of Surgery, Sinai Grace Hospital, Detroit Medical Center, Detroit, Michigan, USA.
Solitary fibrous tumours (SFTs) are rare soft tissue masses that are often clinically silent until they cause mass effect. A paraneoplastic syndrome manifesting as persistent hypoglycaemia, termed Doege-Potter syndrome (DPS), can be associated with these lesions. Surgical treatment is recommended for the management of these tumours.
View Article and Find Full Text PDFSecupyritines A‒C, Three Natural Propellane Securinega Alkaloids: Structure Elucidation and Total Synthesis Based on Biogenetic Building Blocks.
Angew Chem Int Ed Engl
January 2025
Jinan University, State Key Laboratory of Bioactive Molecules and Druggability Assessment, CHINA.
Secupyritines A‒C are unique polycyclic Securinega alkaloids isolated from medicinal plant Flueggea suffruticosa. They feature a distinctive 6/6/6/5/6 fused pentacyclic ring system with a highly strained 2-oxa-6-aza[4.4.
View Article and Find Full Text PDFTotal syntheses of the parvistemoline alkaloids enabled by stereocontrolled Ir/Pd-catalyzed allylic alkylation.
Nat Commun
December 2024
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China.
The functionalized polycycle with densely contiguous tertiary stereocenters is a formidable challenge in synthesizing the parvistemoline family of Stemona alkaloids. We herein report their catalytic, asymmetric total syntheses in 13-14 steps from commercially available 2-(methoxycarbonyl)-pyrrole, featuring the development and deployment of an Ir/Pd-synergistically-catalyzed allylation of α-non-substituted keto esters with secondary aryl-substituted alcohols, stereodivergently accessible to four stereoisomers. Using chiral Pd-enolate and Ir π-allyl complex under neutral conditions, no epimerization occurs.
View Article and Find Full Text PDFDevelopment of a Synthetic Platform for Ent-Pimaranes Reveals their Potential as Novel Non-Redox Active Ferroptosis Inhibitors.
Chemistry
December 2024
Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020, Innsbruck, Austria.
We present a comprehensive account on the evolution of a synthetic platform for a subfamily of ent-pimaranes. For the most complex member, norflickinflimiod C, five distinct strategies relying on either cationic or radical polyene cyclizations to construct the requisite tricyclic carbon scaffold were explored. Insights from early and late stage oxidative and reductive dearomatization studies ultimately led to a mild, rhodium-catalyzed arene hydrogenation for the final synthetic route.
View Article and Find Full Text PDFApplication of β-Keto Acylpyrazoles as 2C Synthons in Asymmetric Cyclizations of -Hydroxychalcones: Stereoselective Construction of -3,4-Dihydrocoumarins.
J Org Chem
December 2024
Institute and State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, P. R. China.
An asymmetric tandem esterification/Michael addition reaction of β-keto acylpyrazoles with -hydroxychalcones has been established under the catalysis of a bifunctional squaramide-tertiary amine. A wide variety of biorelevant 3,4-dihydrocoumarin derivatives were generally obtained in high yields (up to 93%) with excellent diastereo- and enantioselectivities (>19:1 dr, up to 93% ee) under mild reaction conditions. This reaction represents the successful application of β-keto acylpyrazoles as 2C building blocks in catalytic asymmetric cyclizations.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!