The competing enantioselective conversion (CEC) strategy has been extended to cyclic amines. The basis for the CEC approach is the use of two complementary, enantioselective reactions to determine the configuration of the enantiopure substrate. Bode's chiral acylated hydroxamic acids are very effective enantioselective acylating agents for a variety of amines. Pseudoenantiomers of these acyl-transfer reagents were prepared and demonstrated to react with enantiopure cyclic amines with modest to high selectivity. The products were analyzed by ESI-MS to determine selectivity, and the results were used to assign the configuration of the amine substrate. The method was applicable to a variety of cyclic amines as well as primary amines and acyclic secondary amines. The method is limited to amines that are unhindered enough to react with the reagents, and not all amine substitution patters lead to high selectivity.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.7b01748 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
AshPhos Ligand: Facilitating Challenging Aminations in Five- and Six-Membered Heteroaryl Halides Using Cyclic Secondary and Bulky Amines.
JACS Au
January 2025
Department of Chemistry, University of Missouri, 601 South College Avenue, Columbia, Missouri 65211, United States.
Our newly developed AshPhos ligand represents a significant advancement in Buchwald-Hartwig aminations, overcoming many limitations of existing ligands. Created from affordable and accessible materials, AshPhos enhances catalytic performance, especially for extremely difficult substrates, by emphasizing the principles of ligand chelation and cooperativity. Its successful synthesis and application in catalytic aminations underscore its potential for use in the sustainable synthesis of compounds important to medicinal chemistry, materials, and energy.
View Article and Find Full Text PDF-Aminated Octaazaperopyrenedioxides (OAPPDOs) as Precursors for Diazepine and Diazepinone Derivatives.
Org Lett
January 2025
Anorganisch-Chemisches Institut, Universität Heidelberg, 69120 Heidelberg, Germany.
Fully -aminated octaazaperopyrenedioxide (OAPPDO) derivatives have been accessible via Buchwald-Hartwig amination of the -chlorinated starting material. They were isolated as semiquinoidal species with a bent polycyclic core and characterized as nonfluorescent charge-transfer dyes. The corresponding secondary amines were synthesized by reduction and displayed typical absorption and emission behavior for perylene derivatives.
View Article and Find Full Text PDFNovel Nonaqueous PD/PZ/NMP Absorbent for Energy-Efficient CO Capture: Insights into the Crystal-Phase Regulation Mechanism of the Powdery Product.
Environ Sci Technol
January 2025
School of Environmental Science and Engineering, Shenzhen Key Laboratory of Municipal Solid Waste Recycling Technology and Management, Southern University of Science and Technology, Shenzhen 518055, China.
Solid-liquid biphasic absorbents are a promising solution for overcoming the high-energy consumption challenge faced by liquid amine-based CO capture technologies. However, their practical applications are often hindered by difficulties in separating viscous solid-phase products. This study introduces a novel nonaqueous absorbent system (PD/PZ/NMP) composed of 4-amino-1-methylpiperidine (PD), piperazine (PZ), and -methyl-2-pyrrolidone (NMP), engineered to produce easily separable powdery products.
View Article and Find Full Text PDFAmide Derivative of Arjunolic Acid TA-1,4-BiP Enhances ROSmediated Apoptosis in Colorectal Cancer Cells.
Curr Med Chem
January 2025
Department of Chemistry, Sri Sathya Sai Institute of Higher Learning, Puttaparthi, Andhra Pradesh, India.
Introduction: Arjunolic acid, a well-known natural product with various medicinal properties, was isolated from the heartwood of Terminalia arjuna. Various amides of arjunolic acid were synthesized using different aryl and cyclic amines, characterized, and evaluated for their anti-cancer activities at the National Cancer Institute (NCI).
Method: All the derivatives were active against all the cell lines of NCI compared to the parent molecule arjunolic acid.
Anchoring Ag(I) into MOF-253 for Effectively Catalyzing Cycloaddition of CO with Alkynyl Alcohols/Amine under Ambient Conditions.
Inorg Chem
January 2025
Inner Mongolia Engineering Research Centre of Lithium-Sulfur Battery Energy Storage, Inner Mongolia Key Laboratory of Solid State Chemistry for Battery, College of Chemistry and Materials Science, Inner Mongolia Minzu University, Tongliao 028000, People's Republic of China.
In the era of global warming, the conversion of carbon dioxide into high-value products has become a widely scrutinized emerging mitigation strategy. Metalation of bpy-containing MOF-253 led to the synthesis of MOF-253-0.5Ag, which acts as an efficient catalyst for the carbonylative cyclization of CO with alkyne molecules (such as propynyl alcohols and propynyl amines) at room temperature and ambient CO pressure, yielding the corresponding α-alkyl cyclic carbonates and oxazolidinones, thus endowing the catalytic system with bifunctional characteristics.
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!